Acid amide derivatives, process for producing these, and pest control agent containing these

ABSTRACT

The present invention relates to an acid amid derivative of the formula (I) or a salt thereof: 
                         
wherein A is phenyl which may be substituted by X, benzyl which may be substituted by X, naphthyl which may be substituted by X, a heterocyclic group which may be substituted by X, a fused heterocyclic group which may be substituted by X, indanyl (the indanyl may be substituted by halogen, alkyl or alkoxy) or tetrahydronaphthyl (the tetrahydronaphthyl may be substituted by halogen, alkyl or alkoxy), B is alkyl, cycloalkyl, phenyl which may be substituted by Y, a heterocyclic group which may be substituted by Y, or a condensed heterocyclic group which may be substituted by Y, each of R 1  and R 2  is alkyl, cyano or —CO 2 R 14 , or R 1  and R 2  may together form a 3- to 6-membered saturated carbocyclic ring, R 3  is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, —COR 15 , —S(O)mR 16  or —S(O)nNR 17 R 18 , which is useful as an active ingredient of pesticides.

TECHNICAL FIELD

The present invention relates to novel acid amide derivatives useful asactive ingredients for pesticides.

BACKGROUND ART

WO 2001/60783 discloses phenacylamine derivatives, a process for theirproduction and pesticides containing them, but there is no specificdisclosure relating to acid amide derivatives of the formula (I) givenhereinafter.

DISCLOSURE OF THE INVENTION

Over the years, a number of pesticides have been used, but many of themhave various problems such that the effects are inadequate, their use isrestricted as the pests have acquired resistance, they have hightoxicity against human, animal, fish, etc., and their residual effectsdisturb the ecological system. Accordingly, it is desired to developnovel pesticides having high safety without such drawbacks.

Further, parasites on animals are parasitic on the body surfaces,stomachs, intestinal tracts, lungs, hearts, livers, blood vessels,subcutis and lymphatic tissues of domestic animals or companion animalsand thus cause various animal diseases, such as anemia, malnutrition,asthenia, weight loss or disorders of intestinal tract walls, organs orother tissues. Accordingly, it is desired to control such parasites.

The present inventors have conducted various studies on acid amidederivatives to find a superior pesticide. As a result, it has been foundthat novel acid amide derivatives and their salts have very highcontrolling effects against pests at low doses, and they show nosubstantial adverse effects against mammals, fish, etc. The presentinvention has been accomplished on the basis of this discovery. That isthe present invention provides an acid amide derivative of the formula(I) or a salt thereof:

wherein A is phenyl which may be substituted by X, benzyl which may besubstituted by X, naphthyl which may be substituted by X, a heterocyclicgroup which may be substituted by X, a fused heterocyclic group whichmay be substituted by X, indanyl (the indanyl may be substituted byhalogen, alkyl or alkoxy) or tetrahydronaphthyl (the tetrahydronaphthylmay be substituted by halogen, alkyl or alkoxy), B is alkyl, cycloalkyl,phenyl which may be substituted by Y, a heterocyclic group which may besubstituted by Y, or a fused heterocyclic group which may be substitutedby Y, X is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl,haloalkynyl, alkoxy, haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy,alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkenyloxy, haloalkenyloxy,alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio,haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl,haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted byY, phenoxy which may be substituted by Y, benzyloxy which may besubstituted by Y, pyridyloxy which may be substituted by Y, —OR₄, —SR₅,—NR₆R₇, —CO₂R₈, —C(═O)NR₉R₁₀ or an unsaturated heterocyclic group (theunsaturated heterocyclic ring may be substituted by halogen, alkyl,haloalkyl, alkoxy or haloalkoxy), Y is halogen, alkyl, haloalkyl,alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl,haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, —OR₄, —CO₂R₁₁, —CONR₁₂R₁₃ or anunsaturated heterocyclic group (the unsaturated heterocyclic ring may besubstituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each ofR₁ and R₂ is alkyl, cyano or —CO₂R₁₄, or R₁ and R₂ may together form a3- to 6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl, —COR₁₅, —S(O)mR₁₆ or —S(O)nNR₁₇R₁₈, each ofR₄ and R₆ is hydrogen, —C(═W)R₁₉, —C(═W)OR₂₀, —C(═W)SR₂₁, —C(═W)NR₂₂R₂₃,—S(O)qR₂₄ or —S(O)rNR₂₅R₂₆, R₅ is hydrogen, —C(═W)R₁₉, —C(═W)OR₂₀,—C(═W)SR₂₁ or —C(═W)NR₂₂R₂₃, R₇ is hydrogen, alkyl or haloalkyl, each ofR₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃ and R₁₄ is hydrogen or alkyl, R₁₅ ishydrogen, alkyl or alkoxy, each of R₁₆, R₁₇, R₁₈, R₁₉, R₂₀, R₂₁, R₂₂,R₂₃, R₂₄, R₂₅ and R₂₆ is alkyl, haloalkyl or phenyl (the phenyl whichmay be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy),each of m, n, q and r is from 0 to 2, W is oxygen or sulfur, providedthat (1) a case where A is phenyl which may be substituted by X₁, B isalkyl, cycloalkyl, phenyl which may be substituted by Y₁, pyridyl whichmay be substituted by Y₁ or pyrazolyl which may be substituted by Y₁,each of R₁ and R₂ is alkyl, or R₁ and R₂ together form a 3- to6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl, alkylcarbonyl or alkoxycarbonyl, X₁ ishalogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl,alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio,alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,phenyl which may be substituted by Y₁, phenoxy which may be substitutedby Y₁, benzyloxy which may be substituted by Y₁ or pyridyloxy which maybe substituted by Y₁, and Y₁ is halogen, alkyl, haloalkyl, alkoxy,haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro or cyano,and (2) N-[1-methyl-1-(2′-methylisonicotinoyl)ethyl]benzamide, areexcluded; a process for its production; and a pesticide containing it.

The number of substituents X in the phenyl which may be substituted byX, the benzyl which may be substituted by X, the naphthyl which may besubstituted by X, the heterocyclic group which may be substituted by Xor the fused heterocyclic group which may be substituted by X, in A, maybe one or more, and in the case of more than one, such substituents maybe the same or different, and the number of substituents Y in the phenylwhich may be substituted by Y, the heterocyclic group which may besubstituted by Y or the fused heterocyclic group which may besubstituted by Y, in B, or the number of substituents Y in the phenylwhich may be substituted by Y, the phenoxy which may be substituted byY, the benzyloxy which may be substituted by Y or the pyridyloxy whichmay be substituted by Y, in X, may be one or more, and in the case ofmore than one, such substituents may be the same or different. Thenumber of halogen, alkyl or alkoxy which is substituent of indanyl ortetrahydronaphthyl, may be one or more, and in the case of more thanone, such substituents may be the same or different. The number of thesubstituent of the unsaturated heterocyclic group in X or Y, or thenumber of the substituent of the phenyl in R₁₆ to R₂₆, may be one ormore, and in the case of more than one, such substituents may be thesame or different.

The heterocyclic group in A or B, is a 5- or 6-membered heterocyclicgroup containing from 1 to 4 atoms of at least one type selected fromthe group consisting of O, S and N, such as furyl, tetrahydrofuryl,thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, imidazolinyl,imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl,oxadiazolyl, thiadiazolyl, tetrazolyl, pyranyl, pyridyl, piperidinyl,dioxanyl, oxazinyl, morpholinyl, thiazinyl, pyridazinyl, pyrimidinyl,pyrazinyl, piperazinyl or triazinyl.

The fused heterocyclic group in A or B, is a 8- to 10-membered fusedheterocyclic group containing from 1 to 4 atoms of at least one typeselected from the group consisting of O, S and N, such as benzofuranyl,isobenzofuranyl, dihydrobenzofuranyl, dihydroisobenzofuranyl,benzothienyl, isobenzothienyl, dihydrobenzothienyl,dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl,benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl,benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl, isochromanyl,chromonyl, chromanonyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl,quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, imidazopyridyl,naphthyridinyl, pteridinyl, dihydrobenzoxazinyl,dihydrobenzoxazolinonyl, dihydrobenzoxazinonyl or benzothioxanyl.

The unsaturated heterocyclic group in X or Y, is a 5- to 6-memberedunsaturated heterocyclic group containing from 1 to 4 atoms of at. leastone type selected from the group consisting of O, S and N, such asfuryl, thienyl, pyrrolyl, pyrrolinyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, imidazolyl, imidazolinyl, pyrazolyl, pyrazolinyl,triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyranyl, pyridyl,oxazinyl, thiazinyl, pyridazinyl, pyrimidinyl, pyrazinyl, or triazinyl.

The alkyl or alkyl moiety in B, X, Y, R₁ to R₃ or R₇ to R₂₆, the alkylor alkyl moiety as a substituent of indanyl or tetrahydronaphthyl, in A,the alkyl or alkyl moiety as a substituent of unsaturated heterocyclicgroup in X or Y, or, the alkyl or alkyl moiety as a substituent ofphenyl in R₁₆ to R₂₆, may be linear or branched one having from 1 to 6carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl,tert-butyl, pentyl or hexyl.

The cycloalkyl in B may be one having from 3 to 6 carbon atoms, such ascyclopropyl, cyclopentyl or cyclohexyl.

The alkenyl or alkenyl moiety in X may be linear or branched one havingfrom 2 to 7 carbon atoms, such as vinyl, 1-propenyl, allyl, isopropenyl,1-butenyl, 1,3-butadienyl, 1-hexenyl or 1-heptenyl. Further, the alkynylor alkynyl moiety in X may be linear or branched one having from 2 to 7carbon atoms, such as ethynyl, 2-butynyl, 2-pentynyl, 3-hexynyl or4-dimethyl-2-pentynyl.

As the halogen or the halogen as a substituent in A, X, Y, R₇ or R₁₆ toR₂₆ (include halogen as a substituent of indanyl or tetrahydronaphthyl,in A, halogen as a substituent of unsaturated heterocyclic group in Xand Y, and halogen as a substituent of phenyl in R₁₆ to R₂₆), an atom offluorine, chlorine, bromine or iodine may be mentioned. The number ofhalogens as substituents may be one or more, and in a case where it ismore than one, the respective halogens may be the same or different.Further, such halogens may be substituted at any position.

The salt of the acid amide derivative of the above formula (I) may beany salt so long as it is agriculturally acceptable. For example, it maybe an alkali metal salt such as a sodium salt or a potassium salt; analkaline earth metal salt such as a magnesium salt or a calcium salt; anammonium salt such as a dimethylamine salt or a triethylamine salt; aninorganic salt such as a hydrochloride, a perchlorate, a sulfate or anitrate; or an organic salt such as an acetate or a methanesulfonate.

The acid amide derivative of the above formula (I) has various isomerssuch as optical isomers and tautomeric isomers, and the presentinvention includes both isomers and mixtures of such isomers. Further,the present invention also includes various isomers other than the aboveisomers within the common knowledge in the technical field concerned.

The acid amide derivative of the above formula (I) or a salt thereof(hereinafter referred to simply as the compound of the presentinvention) can be produced by the following reactions (A) to (K), or bya usual process for producing a salt.

(II) or a salt thereof (I-1)

In the reaction (A), A, B, R₁, and R₂, are as defined above. Z ishydroxy, alkoxy or halogen, and the halogen may be an atom of fluorine,chlorine, bromine or iodine.

Reaction (A) is carried out usually in the presence of a base and asolvent.

The base may be one or more suitably selected from e.g. an alkali metalsuch as sodium or potassium; an alkali metal alcoholate such as sodiummethylate, sodium ethylate or potassium tertiary butoxide; a carbonatesuch as sodium carbonate or potassium carbonate; a bicarbonate such assodium bicarbonate or potassium bicarbonate; a metal hydroxide such assodium hydroxide or potassium hydroxide; a metal hydride such as sodiumhydride or potassium hydride; an amine such as monomethylamine,dimethylamine or triethylamine; and a pyridine such as pyridine or4-dimethylaminopyridine. The base is used in an amount of from 1 to 3mols, preferably from 1 to 2 mols, per mol of the compound of theformula (II).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile and a ketone such as acetone or methylethyl ketone.

Reaction (A) is carried out, if necessary, in the presence of adehydration condensation agent. The dehydration condensation agent may,for example, be N,N′-dicyclohexylcarbodiimide, chlorosulfonylisocyanate, N,N′-carbonyldiimidazole and trifluoroacetic anhydride.

The reaction temperature for reaction (A) is usually from 0 to 100° C.,preferably from 0 to 50° C., and the reaction time is usually from 0.5to 48 hours, preferably from 1 to 24 hours.

In reaction (B), A, B, R₁ and R₂ are as defined above, and R_(3a) isalkyl, alkoxyalkyl, alkylthioalkyl, —COR₁₅, —S(O)_(m)R₁₆ or—S(O)_(n)NR₁₇R₁₈ (wherein R₁₅, R₁₆, R₁₇, R₁₈, m and n are as definedabove), and T is halogen, and the halogen may be an atom of fluorine,chlorine, bromine or iodine.

Reaction (B) is carried out usually in the presence of a base and asolvent.

The base may be one or more suitably selected from e.g. an alkali metalsuch as sodium or potassium; an alkali metal alcoholate such as sodiummethylate, sodium ethylate or potassium tertiary butoxide; a carbonatesuch as sodium carbonate or potassium carbonate; a bicarbonate such assodium bicarbonate or potassium bicarbonate; a metal hydroxide such assodium hydroxide or potassium hydroxide; a metal hydride such as sodiumhydride or potassium hydride; an amine such as monomethylamine,dimethylamine or triethylamine; and a pyridine such as pyridine or4-dimethylaminopyridine. The base is used in an amount of from 1 to 3mols, preferably from 1 to 1.5 mols, per mol of the compound of theformula (I-1).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; and a ketone such as acetone or methylethyl ketone.

The reaction temperature for reaction (B) is usually from 0 to 100° C.,preferably from 0 to 50° C., and the reaction time is usually from 1 to300 hours, preferably from 1 to 150 hours.

(II) or a salt thereof

In reaction (C), A, R₁ and R₂ are as defined above, and B₁ is phenylsubstituted by —CO₂H, a heterocyclic group substituted by —CO₂H, or afused heterocyclic group substituted by —CO₂H. The formula (V) isanhydrous dicarboxylic acid of Q (phenyl, a heterocyclic group or afused heterocyclic group).

Reaction (C) is carried out usually in the presence of a solvent. Thesolvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxy ethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; and an alcohol such as methanol, ethanol, propanol ortert-butanol.

Reaction (C) is carried out, if necessary, in the presence of a base.The base may be one or more suitably selected from e.g. an alkali metalsuch as sodium or potassium; an alkali metal alcoholate such as sodiummethylate, sodium ethylate or potassium tertiary butoxide; a carbonatesuch as sodium carbonate or potassium carbonate; a bicarbonate such assodium bicarbonate or potassium bicarbonate; a metal hydroxide such assodium hydroxide or potassium hydroxide; a metal hydride such as sodiumhydride or potassium hydride; an amine such as monomethylamine,dimethylamine or triethylamine; and a pyridine such as pyridine or4-dimethylaminopyridine. The base is used in an amount of from 1 to 3mols, preferably from 1 to 1.5 mols, per mol of the compound of theformula (II).

The reaction temperature for reaction (C) is usually from 0 to 150° C.,preferably from 0 to 80° C. The reaction time is usually from 0.5 to 96hours, preferably from 1 to 48 hours.

In reaction (D), A, R₁ and R₂ are as defined above. B₂ is phenylsubstituted by Y₂, a heterocyclic group substituted by Y₂, or a fusedheterocyclic group substituted by Y₂, B₃ is phenyl substituted by Y₃, aheterocyclic group substituted by Y₃, or a fused heterocyclic groupsubstituted by Y₃, Y₂ is an atom of chlorine, bromine or iodine, and Y₃is an unsaturated heterocyclic group (the unsaturated heterocyclic ringmay be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy).

Reaction (D) is carried out usually in the presence of a catalyst, abase, a solvent and an inert gas.

The catalyst may be one or more suitably selected from e.g. palladiumcomplexes such as tetrakis (triphenylphosphine)palladium(0), bis(dibenzylideneacetone)palladium(0), and tris(dibenzylideneacetone)dipalladium(0).

The base may be one or more suitably selected from e.g. a carbonate suchas sodium carbonate, potassium carbonate or calcium carbonate; abicarbonate such as sodium bicarbonate or potassium bicarbonate; and ametal hydroxide such as sodium hydroxide or potassium hydroxide. Thebase is used in an amount of from 1 to 20 mols, preferably from 1 to 10mols, per mol of the compound of the formula (I-4).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; an alcohol such as methanol, ethanol, propanol or tert-butanol;and water.

The inert gas may, for example, be nitrogen gas or argon gas.

The reaction temperature for reaction (D) is usually from 0 to 150° C.,preferably from 15 to 100° C. The reaction time is usually from 0.5 to96 hours, preferably from 1 to 48 hours.

In reaction (E), A, R₁ and R₂ are as defined above, and B₄ is phenylsubstituted by —CO₂H, a heterocyclic group substituted by —CO₂H, or afused heterocyclic group substituted by —CO₂H, B₅ is phenyl substitutedby —CO₂ R_(11a), a heterocyclic group substituted by —CO₂ R_(11a), or afused heterocyclic group substituted by —CO₂ R_(11a), and R_(11a) isalkyl.

The first step in reaction (E) is carried out in the presence of achlorination agent. The chlorination agent may be one or more suitablyselected from e.g. thionyl chloride, oxalyl chloride and phosphoruspentachloride.

The first step in reaction (E) is carried out, if necessary, in thepresence of a solvent. The solvent may be any solvent so long as it is asolvent inert to the reaction. For example, it may be one or moresuitably selected from e.g. an aromatic hydrocarbon such as benzene,toluene, xylene or chlorobenzene; an aliphatic hydrocarbon such ascarbon tetrachloride, methyl chloride, chloroform, dichloromethane,dichloroethane, trichloroethane, hexane or cyclohexane; an ether such asdioxane, tetrahydrofuran, diethyl ether or dimethoxyethane; and an estersuch as methyl acetate or ethyl acetate.

The reaction temperature for the first step in reaction (E) is usuallyfrom 0 to 200° C., preferably from 15 to 150° C. The reaction time isusually from 0.1 to 72 hours, preferably from 0.5 to 3 hours.

The second step in reaction (E) is carried out, if necessary, in thepresence of a base. The base may be one or more suitably selected frome.g. an alkali metal such as sodium or potassium; an alkali metalalcoholate such as sodium methylate, sodium ethylate or potassiumtertiary butoxide; a carbonate such as sodium carbonate or potassiumcarbonate; a bicarbonate such as sodium bicarbonate or potassiumbicarbonate; a metal hydroxide such as sodium hydroxide or potassiumhydroxide; a metal hydride such as sodium hydride or potassium hydride;an amine such as monomethylamine, dimethylamine or triethylamine; and apyridine such as pyridine or 4-dimethylaminopyridine. The base is usedin an amount of from 1 to 5 mols, preferably from 1 to 2 mols, per molof the compound of the formula (I-6).

The second step in reaction (E) is carried out, if necessary, in thepresence of a solvent. The solvent may be any solvent so long as it is asolvent inert to the reaction. For example, it may be one or moresuitably selected from e.g. an aromatic hydrocarbon such as benzene,toluene, xylene or chlorobenzene; an aliphatic hydrocarbon such ascarbon tetrachloride, methyl chloride, chloroform, dichloromethane,dichloroethane, trichloroethane, hexane or cyclohexane; an ether such asdioxane, tetrahydrofuran, diethyl ether or dimethoxyethane; an estersuch as methyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; and a ketone such as acetone or methylethyl ketone. Further, in this reaction, the compound of the formula(VII) may serve also as a solvent if used excessively.

The reaction temperature for the second step in reaction (E) is usuallyfrom 0 to 100° C., preferably from 0 to 50° C. The reaction time isusually from 0.1 to 48 hours, preferably from 0.5 to 6 hours.

In reaction (F), A, B₄ B₅, R₁, R₂ and B_(11a) are as defined above.

Reaction (F) is carried out usually in the presence of a catalyst or adehydration condensation agent.

The catalyst may be one or more suitably selected from e.g. a mineralacid such as hydrochloric acid or sulfuric acid; an organic acid such asparatoluene sulfonic acid; and a Lewis acid such as boron trifluorideetherate.

The dehydration condensation agent may be one or more suitably selectedfrom e.g. N,N′-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate,N,N′-carbonyldiimidazole and trifluoroacetic anhydride.

Reaction (F) is carried out, if necessary, in the presence of a solvent.The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; and an alcohol such as methanol, ethanol, propanol ortert-butanol. Further, in this reaction, the compound of the formula(VII) may serve also as a solvent if used excessively.

The reaction temperature for reaction (F) is usually from 0 to 200° C.,preferably from 0 to 100° C. The reaction time is usually from 0.1 to 96hours, preferably from 0.5 to 24 hours.

In reaction (G), A, B₄, R₁, R₂, R₁₂ and R₁₃ are as defined above, and B₆is phenyl substituted by —CONR₁₂R₁₃, a heterocyclic group substituted by—CONR₁₂R₁₃, or a fused heterocyclic group substituted by —CONR₁₂R₁₃(wherein R₁₂ and R₁₃ are as defined above)

The first step in reaction (G) is carried out in accordance with thefirst step in the above-described reaction (E).

The second step in the reaction (G) is carried out, if necessary, in thepresence of a base. The base may be one or more suitably selected frome.g. an alkali metal such as sodium or potassium; an alkali metalalcoholate such as sodium methylate, sodium ethylate or potassiumtertiary butoxide; a carbonate such as sodium carbonate or potassiumcarbonate; a bicarbonate such as sodium bicarbonate or potassiumbicarbonate; a metal hydroxide such as sodium hydroxide or potassiumhydroxide; a metal hydride such as sodium hydride or potassium hydride;an amine such as monomethylamine, dimethylamine or triethylamine; and apyridine such as pyridine or 4-dimethylaminopyridine. The base is usedin an amount of from 1 to 10 mols, preferably from 1 to 2 mols, per molof the compound of the formula (I-6).

The second step in reaction (G) is carried out, if necessary, in thepresence of a solvent. The solvent may be any solvent so long as it is asolvent inert to the reaction. For example, it may be one or moresuitably selected from e.g. an aromatic hydrocarbon such as benzene,toluene, xylene or chlorobenzene; an aliphatic hydrocarbon such ascarbon tetrachloride, methyl chloride, chloroform, dichloromethane,dichloroethane, trichloroethane, hexane or cyclohexane; an ether such asdioxane, tetrahydrofuran, diethyl ether or dimethoxyethane; an estersuch as methyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; and water.

The reaction temperature for the second step in reaction (G) is usuallyfrom 0 to 100° C., preferably from 0 to 50° C. The reaction time isusually from 0.1 to 48 hours, preferably from 0.5 to 6 hours.

In reaction (H), A, B₄, B₆, R₁, R₂, R₁₂ and B₁₃ are as defined above.

Reaction (H) is carried out usually in the presence of a dehydrationcondensation agent and a solvent.

The dehydration condensation agent may be one or more suitably selectedfrom e.g. N,N′-dicyclohexylcarbodiimide, chlorosulfonyl isocyanate,N,N′-carbonyldiimidazole and trifluoroacetic anhydride.

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; and a ketone such as acetone or methylethyl ketone.

The reaction temperature for the reaction (H) is usually from 0 to 200°C., preferably from 0 to 100° C. The reaction time is usually from 0.1to 96 hours, preferably from 0.5 to 24 hours.

In reaction (I), A, B₅, B₆, R₁, R₂, R₁₂ and R₁₃ are as defined above.

Reaction (I) is carried out usually in the presence of a solvent. Thesolvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; an alcohol such as methanol, ethanol, propanol or tert-butanol;and water. Further, in this reaction, the compound of the formula (VIII)may serve also as a solvent if used excessively.

The reaction temperature for the reaction (I) is usually from 0 to 150°C., preferably from 0 to 80° C. The reaction time is usually from 0.1 to48 hours, preferably from 0.5 to 24 hours.

In reaction (J), B is as defined above, A₁ is phenyl substituted by—OR_(4a), benzyl substituted by —OR_(4a), naphthyl substituted by—OR_(4a), a heterocyclic group substituted by —OR_(4a) or a fusedheterocyclic group substituted by —OR_(4a), A₂ is phenyl substituted by—OH, benzyl substituted by —OH, naphthyl substituted by —OH, aheterocyclic group substituted by —OH or a fused heterocyclic groupsubstituted by —OH, each of R_(1a) and R_(2a) is alkyl or cyano. R_(1a)and R_(2a) may together form a 3- to 6-membered saturated carbocycle,R_(4a) is —C(═W)R₁₉, —C(═W)OR₂₀, —C(═W)SR₂₁, —C(═W)NR₂₂R₂₃, —S(O)qR₂₄ or—S(O)rNR₂₅R₂₆ (wherein R₁₉ to R₂₆, W, q and r are as defined above), andM is sodium or potassium.

Reaction (J) is usually carried out in the presence of a solvent. Thesolvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; a polar aproticsolvent such as dimethyl sulfoxide, sulfolane, dimethylacetamide,dimethylformamide, N-methylpyrrolidone or pyridine; a nitrile such asacetonitrile, propionitrile or acrylonitrile; a ketone such as acetoneor methyl ethyl ketone;an alcohol such as methanol, ethanol, propanol ortert-butanol; and water.

The reaction temperature for reaction (J) is usually from 0 to 100° C.,preferably from 20 to 80° C. The reaction time is usually from 0.1 to 24hours, preferably from 0.1 to 12 hours.

In reaction (K), A₁, A₂, B, R_(1a), R_(2a) and R_(4a) are as definedabove, G is an atom of chlorine, bromine or iodine.

Reaction (K) is usually carried out in the presence of a base and asolvent.

The base may be one or more suitably selected from e.g. an alkali metalalcoholate such as sodium methylate, sodium ethylate or potassiumtertiary butoxide; a carbonate such as sodium carbonate or potassiumcarbonate; a bicarbonate such as sodium bicarbonate or potassiumbicarbonate; a metal hydroxide such as sodium hydroxide or potassiumhydroxide; a metal hydride such as sodium hydride or potassium hydride;an amine such as monomethylamine, dimethylamine or triethylamine; and apyridine such as pyridine or 4-dimethylaminopyridine. The base is usedin an amount of from 1 to 2 mols, preferably from 1 to 1.5 mols, per molof the compound of the formula (I-10).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; and a ketone such as acetone or methylethyl ketone.

The reaction temperature for reaction (K) is usually from −20 to 100°C., preferably from 0 to 50° C. The reaction time is usually from 0.1 to24 hours, preferably from 0.1 to 12 hours.

The compound of the formula (II) to be used in the above reaction (A) or(C) is novel and can be produced by the following reactions (L) to (N).

In reaction (L), A, R₁ and R₂ are as defined above. In reaction (L), asalt of the compound (II) can be produced by post treatment of thereaction or in accordance with a usual reaction for forming a salt.

Reaction (L) is carried out usually in the presence of an oxidizingagent and a solvent.

The oxidizing agent may, for example, be potassium ferricyanide. Theoxidizing agent is used in an amount of from 1 to 10 mols, preferablyfrom 1 to 5 mols, per mol of the compound of the formula (XII).

The solvent may be any solvent so long as it is inert to the reaction.For example, it may be one or more suitably selected from e.g. an ethersuch as dioxane, tetrahydrofuran, diethyl ether or dimethoxyethane; anester such as methyl acetate or ethyl acetate; a polar aprotic solventsuch as dimethyl sulfoxide, sulfolane, dimethylacetamide,dimethylformamide, N-methylpyrrolidone or pyridine; a nitrile such asacetonitrile, propionitrile or acrylonitrile; a ketone such as acetoneor methyl ethyl ketone; and water.

The reaction temperature for reaction (L) is usually from 20 to 150° C.,preferably from 50 to 100° C. The reaction time is usually from 0.5 to30 hours, preferably from 1 to 20 hours.

In reaction (M), A, R₁ and R₂ are as defined above. In reaction (M), asalt of the compound (II) can be roduced by post treatment of thereaction or in accordance with a usual reaction for forming a salt.

The cyclization reaction in reaction (M) is carried out usually in thepresence of a base and a solvent.

The base may be one or more suitably selected from e.g. an alkali metalsuch as sodium or potassium; an alkali metal alcoholate such as sodiummethylate, sodium ethylate or potassium tert-butoxide; and a metalhydride such as sodium hydride or potassium hydride. The base is used inan amount of from 1 to 3 mols, preferably from 1 to 1.5 mols per mol ofthe compound of the formula (XIII).

The solvent may be any solvent so long as it is inert to the reaction.For example, it may be one or more suitably selected from e.g. anaromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene;an ether such as dioxane, tetrahydrofuran, diethyl ether ordimethoxyethane; an alcohol such as methanol, ethanol, propanol ortert-butanol; and a nitrile such as acetonitrile, propionitrile oracrylonitrile.

The reaction temperature for the cyclization reaction in reaction (M) isusually from 0 to 150° C., preferably from 30 to 100° C. The reactiontime is usually from 0.5 to 24 hours, preferably from 1 to 12 hours.

The hydrolytic reaction in reaction (M) may be carried out in accordancewith a common hydrolytic reaction and is carried out usually in thepresence of an acid or base and a solvent.

The acid may, for example, be hydrogen chloride or sulfuric acid. Thebase may, for example, be a metal hydroxide such as sodium hydroxide orpotassium hydroxide.

The solvent may be any solvent so long as it is inert to the reaction.For example, it may be one or more suitably selected e.g. an alcoholsuch as methanol, ethanol, propanol or tert-butanol; a nitrile such asacetonitrile, propionitrile or acrylonitrile; a ketone such as acetoneor methyl ethyl ketone; and water.

The reaction temperature for the hydrolytic reaction in reaction (M) isusually from 0 to 100° C., preferably from 20 to 80° C. The reactiontime is usually from 0.1 to 12 hours, preferably from 0.1 to 1 hour.

In reaction (N), A, R₁ and R₂ are as defined above. In reaction (N), asalt of the compound (II) can be produced by post treatment of thereaction or in accordance with a usual reaction for forming a salt.

The reduction reaction in reaction (N) may, for example, be catalyticreduction, reduction by a metal hydride (such as sodium boron hydride,or lithium aluminum hydride) or reduction by e.g. triphenylphosphine orsulfide. The catalytic reduction is usually carried out by reacting withhydrogen, formic acid, ammonium formate, an alcohol, cyclohexane,triethylammonium formate or ammonium chloride, in the presence of acatalyst. The catalyst may be one or more suitably selected from e.g.platinum, platinum oxide, platinum black, Raney Nickel, palladium,palladium-carbon, rhodium, rhodium-alumina, iron and copper.

Reaction (N) is carried out usually in the presence of a solvent. Thesolvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene or xylene; an aliphatichydrocarbon such as hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; an alcohol such as methanol, ethanol, propanol or tert-butanol;and water.

The reaction temperature in reaction (N) is usually from 0 to 150° C.,preferably from 0 to 80° C. The reaction time is usually from 0.5 to 96hours, preferably from 1 to 48 hours.

The compound of the formula (XIII) to be used in the above reaction (M)is novel and can be produced by the following reaction (O).

In reaction (O), A, R₁ and R₂ are as defined above.

Reaction (O) may be carried out, if necessary, in the presence of asolvent. The solvent may be any solvent so long as it is inert to thereaction, and for example, it may be one or more suitably selected frome.g. an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,chloroform, dichloromethane, dichloroethane, trichloroethane, hexane orcyclohexane; an ether such as dioxane, tetrahydrofuran, diethyl ether ordimethyoxyethane; an ester such as methyl acetate or ethyl acetate; analcohol such as methanol, ethanol, propanol or tert-butanol; a nitrilesuch as acetonitrile, propionitrile or acrylonitrile; and a ketone suchas acetone or methyl ethyl ketone.

Methyl iodide in reaction (O) is used in an amount of from 1 to 10 mols,preferably from 1 to 3 mols, per mol of the compound of the formula(XV). Further, methyl iodide may serve also as a solvent if usedexcessively.

The reaction temperature for reaction (O) is usually from 0 to 100° C.,preferably from 10 to 50° C. The reaction time is usually from 0.5 to 48hours, preferably from 1 to 24 hours.

The compound of the formula (XIV) to be used in the above reaction (N)is novel and can be produced by the following reaction (P).

In reaction (P), A, R₁ and R₂ are as defined above, U is an atom ofchlorine or bromine.

Reaction (P) is carried out in the presence of an azidation agent. Theazidation agent may be one or more suitably selected from e.g. sodiumazide, potassium azide and trimethylsilyl azide.

Reaction (P) is carried out usually in the presence of a solvent. Thesolvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; a nitrile such as acetonitrile,propionitrile or acrylonitrile; a ketone such as acetone or methyl ethylketone; an alcohol such as methanol, ethanol, propanol or tert-butanol;and water.

The reaction temperature for reaction (P) is usually from 0 to 150° C.,preferably from 20 to 90° C. The reaction time is usually from 0.1 to 96hours, preferably from 0.5 to 12 hours.

The compound of the formula (XV) to be used in the above reaction (O) isnovel and can be produced by the following reaction (Q).

In reaction (Q), A, R₁ and R₂ are as defined above.

Reaction (Q) can be carried out in accordance with a common hydrazonesynthetic reaction and, if necessary, in the presence of a dehydratingagent and/or a catalyst.

As the dehydrating agent, molecular sieve may, for example, bementioned. The dehydrating agent may be used usually from 1 to 30 times,preferably from 5 to 10 times relative to the weight of the compound ofthe formula (XII).

The catalyst may, for example, be titanium tetrachloride.

Dimethylhydrazine for reaction (Q) is used usually in an amount of from1 to 30 mols, preferably from 5 to 10 mols, per mol of the compound ofthe formula (XII).

The reaction temperature for reaction (Q) is usually from 20 to 150° C.,preferably from 50 to 120° C. The reaction time is usually from 5 to 200hours, preferably from 24 to 120 hours.

The compound of the formula (XVI) to be used in the above reaction (P)is novel and can be produced by the following reaction (R).

In reaction (R), A, R₁, R₂ and U are as defined above.

Reaction (R) is carried out in the presence of a chlorination agent or abromination agent. The chlorination agent may be one or more suitablyselected from e.g. chlorine and N-chlorosuccinimide. The brominationagent may be one or more suitably selected from e.g. bromine,N-bromosuccinimide and phenyltrimethyl ammonium tribromide.

Reaction (R) is carried out usually in the presence of a solvent. Thesolvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; an aliphatic hydrocarbon such as carbon tetrachloride,methyl chloride, chloroform, dichloromethane, dichloroethane,trichloroethane, hexane or cyclohexane; an ether such as dioxane,tetrahydrofuran, diethyl ether or dimethoxyethane; an ester such asmethyl acetate or ethyl acetate; a polar aprotic solvent such asdimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide,N-methylpyrrolidone or pyridine; an organic acid such as acetic acid orpropionic acid; and water.

Reaction (R) is carried out, if necessary, in the presence of a base oran acid.

The base may, for example, be lithium diisopropylamide. The base is usedin an amount of from 1 to 2 mols, preferably from 1 to 1.2 mols, per molof the compound of the formula (XII).

The acid may be one or more suitably selected from e.g. an organic acidsuch as acetic acid or propionic acid, and aluminum chloride. The acidis usually used in a catalytic amount. Further, an organic acid as asolvent may serve as both a solvent and an acid if used excessively.

The reaction temperature for reaction (R) is usually from −100 to 150°C., preferably from −78 to 110° C. The reaction time is usually from 0.1to 48 hours, preferably from 0.5 to 24 hours. However, if it is carriedout in the presence of a base, the reaction temperature is usually from−100 to 0° C., preferably from −78 to −20° C., and the reaction time isusually from 0.1 to 12 hours, preferably from 0.5 to 6 hours. If it iscarried out in the presence of an acid, the reaction temperature isusually from 0 to 150° C., preferably from 20 to 110° C., and thereaction time is usually from 0.1 to 48 hours, preferably from 1 to 24hours.

The compound of the formula (XII) to be used in the above reaction (Q)is a known compound, or can be produced by the following reactions (S)to (T) or by methods in accordance therewith.

In reaction (S), R₁ and R₂ are as defined above, and Z is an oxygen atomor —C(G₁)G₂-, Xa is an hydrogen atom, chlorine atom or alkyl, Xa′ is achlorine atom or alkyl, each of Xb, Xc, Xd, Xe, G₁ and G₂ is an atom ofhydrogen, fluorine or chlorine, V is an atom of bromine or iodine, and jis 0 or 1.

The first step in reaction (S) is carried out in the presence of a baseand a solvent.

The base may be suitably selected from an organic lithium compound suchas lithium diisopropylamide. The base is used in an amount of from 1 to2 mols, preferably from 1 to 1.5 mols, per mol of the compound of theformula (XVII).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an ether such as dioxane, tetrahydrofuran and diethyl ether.

The chlorination agent to be used for the first step in reaction (S)may, for example, be N-chlorosuccinimide.

The formula: Xa′-I to be used for the first step in reaction (S) is usedin an amount of from 1 to 10 mols, preferably from 1 to 5 mols, per molof the compound of the formula (XVII). Further, the chlorination agentto be used for the first step in reaction (S) is used in an amount offrom 1 to 5 mols, preferably from 1 to 3 mols, per mol of the compoundof the formula (XVII).

The first step in reaction (S) is carried out, if necessary, in thepresence of an inert gas. The inert gas may be suitably selected frome.g. nitrogen gas or argon gas.

The reaction temperature for the first step in reaction (S) is usuallyfrom −100 to 50° C., preferably from −70 to 25° C. The reaction time isusually from 1 to 48 hours, preferably from 1 to 20 hours.

The second step in reaction (S) is carried out, usually in the presenceof a base and a solvent.

The base may be one or more suitably selected from e.g. organic lithiumcompounds such as methyllithium and n-butyllithium. The base is used inan amount of from 1 to 2 mols, preferably from 1 to 1.5 mols, per mol ofthe compound of the formula (XVII) or (XVIII).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.ethers such as dioxane, tetrahydrofuran and diethyl ether.

The compound of the formula (XIX) to be used for the second step inreaction (S) is used in an amount of from 1 to 3 mols, preferably from 1to 1.5 mols, per mol of the compound of the formula (XVII) or (XVIII).

The second step in reaction (S) is carried out, if necessary, in thepresence of an inert gas. The inert gas may be suitably selected frome.g. nitrogen gas and argon gas.

The reaction temperature for the second step in reaction (S) is usuallyfrom −100 to 50° C., preferably from −70 to 25° C. The reaction time isusually from 1 to 48 hours, preferably from 1 to 20 hours.

In reaction (T), R₁, R₂, Z, Xa, Xa′, Xb, Xc, Xd, Xe, V and j are asdefined above.

The first step in reaction (T) is carried out usually in the presence ofa base and a solvent.

The base may be one or more suitably selected from e.g. organic lithiumcompounds such as methyllithium and n-butyllithium.

The base is used in an amount of from 1 to 2 mols, preferably from 1 to1.5 mols, per mol of the compound of the formula (XVII) or (XVIII).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an ether such as dioxane, tetrahydrofuran and diethyl ether.

The compound of the formula (XX) to be used for the first step inreaction (T) is used in an amount of from 1 to 3 mols, preferably from 1to 1.5 mols, per mol of the compound of the formula (XVII) or (XVIII).

The first step in reaction (T) is carried out, if necessary, in thepresence of an inert gas. The inert gas may be suitably selected frome.g. nitrogen gas and argon gas.

The reaction temperature for the first step in reaction (T) is usuallyfrom −100 to 50° C., preferably from −70 to 25° C. The reaction time isusually from 1 to 48 hours, preferably from 1 to 20 hours.

The second step for reaction (T) is carried out usually in the presenceof an oxidizing agent and a solvent.

The oxidizing agent may be one or more suitably selected from e.g.pyridinium chlorochromate and manganese dioxide. The oxidizing agent isused in an amount of from 1 to 10 mols, preferably from 1 to 3 mols, permol of the compound of the formula (XXI).

The solvent may be any solvent so long as it is a solvent inert to thereaction. For example, it may be one or more suitably selected from e.g.an aromatic hydrocarbon such as benzene, toluene, xylene orchlorobenzene; and an aliphatic hydrocarbon such as carbontetrachloride, methyl chloride, chloroform, dichloromethane,dichloroethane, trichloroethane, hexane or cyclohexane.

The reaction temperature for the second step in reaction (T) is usuallyfrom 0 to 150° C., preferably from to 100° C. The reaction time isusually from 0.5 to 24 hours, preferably from 1 to 12 hours.

Preferred embodiments of pesticides containing the compounds of thepresent invention will now be described.

The pesticides containing the compounds of the present invention areparticularly useful as an insecticide, a miticide, a nematicide and asoil pesticide, and they are effective for controlling plant parasiticmites such as two-spotted spider mite (Tetranychus urticae), carminespider mite (Tetranychus cinnabarinus), kanzawa spider mite (Tetranychuskanzawai), citrus red mite (Panonychus citri), European red mite(Panonychus ulmi), broad mite (Polyphagotarsonemus latus), pink citrusrust mite (Aculops pelekassi) and bulb mite (Rhizoglyphus echinopus);agricultural insect pests such as aphids such as green peach aphid(Myzus persicae) and cotton aphid (Aphis gossypii), diamondback moth(Plutella xylostella), cabbage armyworm (Mamestra brassicae), commoncutworm (Spodoptera litura), codling moth (Laspeyresia pomonella),bollworm (Heliothis zea), tobacco budworm (Heliothis virescens), gypsymoth (Lymantria dispar), rice leafroller (Cnaphalocrocis medinalis),Adoxophyes sp., colorado potato beetle (Leptinotarsa decemlineata),cucurbit leaf beetle (Aulacophora femoralis), boll weevil (Anthonomusgrandis), planthoppers, leafhoppers, scales, bugs, whiteflies, thrips,grasshoppers, anthomyiid flies, scarabs, black cutworm (Agrotisipsilon), cutworm (Agrotis segetum) and ants; plant parasitic nematodessuch as root-knot nematodes, cyst nematodes, root-lesion nematodes, ricewhite-tip nematode (Aphelenchoides besseyi), strawberry bud nematode(Nothotylenchus acris), pine wood nematode (Bursaphelenchus lignicolus);gastropods such as slugs and snails; soil pests such as isopods such aspillbugs (Armadilidium vulgare) and pillbugs (Porcellio scaber);hygienic insect pests such as tropical rat mite (Ornithonyssus bacoti),cockroachs, housefly (Musca domestica) and house mosquito (Culexpipiens); stored grain insect pests such as angoumois grai moth(Sitotroga cerealella), adzuki bean weevil (Callosobruchus chinensis),red flour beetle (Tribolium castaneum) and mealworms; household goodsinsect pests such as casemaking clothes moth (Tinea pellionella), blackcarpet beetle (Anthrenus scrophularidae) and subterranean termites;domestic mites such as mold mite (Tyrophagus putrescentiae),Dermatophagoides farinae and Chelacaropsis moorei. Among them, thepesticides containing the compounds of the present invention areparticularly effective for controlling agricultural insect pests, plantparasitic nematodes or the like. Further, they are effective againstinsect pests having acquired resistance to organophosphorus, carbamateand/or synthetic pyrethroid insecticides. Moreover, the compounds of thepresent invention have excellent systemic properties, and by theapplication of the compounds of the present invention to soil treatment,not only noxious insects, noxious mites, noxious nematodes, noxiousgastropods and noxious isopods in soil but also foliage pests can becontrolled.

Another preferred embodiments of the pesticides containing compounds ofthe present invention may be agricultural and horticultural pesticideswhich collectively control the above-mentioned plant parasitic mites,agricultural insect pests, plant parasitic nematodes, gastropods andsoil pests.

The pesticide containing the compound of the present invention, isusually formulated by mixing the compound with various agriculturaladjuvants and used in the form of a formulation such as a dust,granules, water-dispersible granules, a wettable powder, a water-basedsuspension concentrate, an oil-based suspension concentrate, watersoluble granules, an emulsifiable concentrate, a soluble concentrate, apaste, an aerosol or an ultra low-volume formulation. However, so longas it is suitable for the purpose of the present invention, it may beformulated into any type of formulation which is commonly used in thisfield. Such agricultural adjuvants include solid carriers such asdiatomaceous earth, slaked lime, calcium carbonate, talc, white carbon,kaoline, bentonite, a mixture of kaolinite and sericite, clay, sodiumcarbonate, sodium bicarbonate, mirabilite, zeolite and starch; solventssuch as water, toluene, xylene, solvent naphtha, dioxane, acetone,isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane,dimethylsulfoxide, dimethylformamide, dimethylacetamide,N-methyl-2-pyrrolidone, and alcohol; anionic surfactants and spreaderssuch as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, adialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acidester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ethersulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, analkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, analkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt ofalkylphosphoric acid ester, an alkylaryl phosphate, a styrylarylphosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, apolyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylenealkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl etherphosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester,and a salt of a condensate of naphthalene sulfonate with formalin;nonionic surfactants and spreaders such as a sorbitan fatty acid ester,a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acidalcohol polyglycol ether, acetylene glycol, acetylene alcohol, anoxyalkylene block polymer, a polyoxyethylene alkyl ether, apolyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, apolyoxyethylene glycol alkyl ether, a polyoxyethylene fatty acid ester,a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerinfatty acid ester, a polyoxyethylene hydrogenated castor oil, and apolyoxypropylene fatty acid ester; and vegetable and mineral oils suchas olive oil, kapok oil, castor oil, palm oil, camellia oil, coconutoil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil,soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffins.Such adjuvants may be selected for use among those known in this field,so long as the purpose of the present invention can thereby beaccomplished. Further, various additives which are commonly used, suchas a filler, a thickener, an anti-settling agent, an anti-freezingagent, a dispersion stabilizer, a phytotoxicity reducing agent, and ananti-mold agent, may also be employed.

The weight ratio of the compound of the present invention to the variousagricultural adjuvants is usually from 0.001:99.999 to 95:5, preferablyfrom 0.005:99.995 to 90:10.

In the actual application of such a formulation, it may be used as itis, or may be diluted to a predetermined concentration with a diluentsuch as water, and various spreaders may be added thereto, as the caserequires.

The application of the pesticide containing the compound of the presentinvention can not generally be defined, as it varies depending upon theweather conditions, the type of the formulation, the application season,the application site or the types or degree of outbreak of the pestinsects. However, it is usually applied in a concentration of the activeingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to500,000 ppm, and the dose per unit area is such that the compound of thepresent invention is from 0.05 to 50,000 g, preferably from 1 to 30,000g, per hectare. Further, agricultural and horticultural pesticides asanother preferred embodiment of pesticides containing the compounds ofthe present invention may be applied in accordance with theabove-described application of pesticides. The present inventionincludes such a method for controlling pests, particularly forcontrolling agricultural insect pests or plant parasitic nematodes bysuch applications.

Various formulations of pesticides containing the compounds of thepresent invention or their diluted compositions may be applied byconventional methods for application which are commonly employed, suchas spraying (e.g. spraying, jetting, misting, atomizing, powder or grainscattering or dispersing in water), soil application (e.g. mixing ordrenching), surface application (e.g. coating, powdering or covering) orimpregnation to obtain poisonous feed. Further, it is possible to feeddomestic animals with a food containing the above active ingredient andto control the outbreak or growth of pests, particularly insect pests,with their excrements. Furthermore, the active ingredient may also beapplied by a so-called ultra low-volume application method. In thismethod, the composition may be composed of 100% of the activeingredient.

Further, the pesticides containing compounds of the present inventionmay be mixed with or may be used in combination with other agriculturalchemicals, fertilizers or phytotoxicity-reducing agents, wherebysynergistic effects or activities may sometimes be obtained. Such otheragricultural chemicals include, for example, a herbicide, aninsecticide, a miticide, a nematicide, a soil pesticide, a fungicide, anantivirus agent, an attractant, an antibiotic, a plant hormone and aplant growth regulating agent. Especially, with a mixed pesticide havinga compound of the present invention mixed with or used in combinationwith one or more active compounds of other agricultural chemicals, theapplication range, the application time, the pesticidal activities, etc.may be improved to preferred directions. The compound of the presentinvention and the active compounds of other agricultural chemicals mayseparately be formulated so that they may be mixed for use at the timeof application, or they may be formulated together. The presentinvention includes such a mixed pesticidal composition.

The mixing ratio of the compound of the present invention to the activecompounds of other agricultural chemicals can not generally be defined,since it varies depending upon the weather conditions, the types offormulations, the application time, the application site, the types ordegree of outbreak of insect pests, etc., but it is usually within arange of from 1:300 to 300:1, preferably from 1:100 to 100:1, by weight.Further, the dose for the application is such that the total amount ofthe active compounds is from 0.1 to 50,000 g, preferably from 1 to30,000 g, per hectare. The present invention includes a method forcontrolling pests by an application of such a mixed pesticidecomposition.

The active compounds of pest control agents such as insecticides,miticides, nematicides or soil pesticides in the above-mentioned otheragricultural chemicals, include, for example, (by common names, some ofthem are still in an application stage) organic phosphate compounds suchas Profenofos, Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon,Chlorpyrifos-methyl, Acephate, Prothiofos, Fosthiazate, Phosphocarb,Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, andMethamidophos; carbamate compounds such as Carbaryl, Propoxur, Aldicarb,Carbofuran, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimicarb,Fenobucarb, Carbosulfan, and Benfuracarb; nereistoxin derivatives suchas Cartap, Thiocyclam and Bensultap; organic chlorine compounds such asDicofol, and Tetradifon; organometallic compounds such as FenbutatinOxide; pyrethroid compounds such as Fenvalerate, Permethrin,Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, Ethofenprox andBifenthrin; benzoylurea compounds such as Diflubenzuron, Chlorfluazuron,Teflubenzuron, Flufenoxuron, Lufenuron, and Novaluron; juvenilehormone-like compounds such as Methoprene, Pyriproxyfen, and Fenoxycarb;pyridazinone compounds such as Pyridaben; pyrazole compounds such asFenpyroximate, Fipronil, Tebufenpyrad, Ethiprole, Tolfenpyrad, andAcetoprole; neonicotinoids such as Imidacloprid, Nitenpyram,Acetamiprid, Thiacloprid, Thiamethoxam, Clothianidin, and Dinotefuran;hydrazine compounds such as Tebufenozide, Methoxyfenozide, andChromafenozide; dinitro compounds; organic sulfur compounds; ureacompounds; triazine compounds; hydrazone compounds; and other compounds,such as Flonicamid, Buprofezin, Hexythiazox, Amitraz, Chlordimeform,Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr,Indoxacarb, Acequinocyl, Etoxazole, Cyromazine, 1,3-dichloropropene,Diafenthiuron, Benclothiaz, Flufenerim, Pyridalyl, and Spirodiclofen.Further, microbial agricultural chemicals such as BT agents, insectviruses, entomopathogenic fungi, and nematophagous fungi or antibioticssuch as Avermectin, Milbemectin, Spinosad, Ivermectin, andEmamectin-benzoate may be used in admixture or in combination.

The active compounds of fungicides among the above-mentioned otheragricultural chemicals include, for example, (by common names, some ofwhich are still in an application stage) pyrimidinamine compounds suchas Mepanipyrim, Pyrimethanil, and Cyprodinil; azole compounds such asTriadimefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole,Penconazole, Flusilazole, Myclobutanil, Cyproconazole, Terbuconazole,Hexaconazole, Furconazole-cis, Prochloraz, Metconazole, Epoxiconazole,Tetraconazole, Oxpoconazole, and Sipconazole; quinoxaline compounds suchas Quinomethionate; dithiocarbamate compounds such as Maneb, Zineb,Mancozeb, Polycarbamate, Propineb; organic chlorine compounds such asFthalide, Chlorothalonil, and Quintozene; imidazole compounds such asBenomyl, Thiophanate-Methyl, Carbendazim, and Cyazofamid; pyridinaminecompounds such as Fluazinam; cyanoacetamide compounds such as Cymoxanil;phenylamide compounds such as Metalaxyl, Oxadixyl, Ofurace, Benalaxyl,Furalaxyl, and Cyprofuram; sulfenic acid compounds such asDichlofluanid; copper compounds such as cupric hydroxide, and OxineCopper; isoxazole compounds such as Hydroxyisoxazole; organophosphoruscompounds such as Fosetyl-Al, Tolclofos-Methyl, S-benzylO,O-diisopropylphosphorothioate, O-ethyl S,S-diphenylphosphorodithioate,and aluminumethylhydrogen phosphonate; N-halogenothioalkyl compoundssuch as Captan, Captafol, and Folpet; dicarboximide compounds such asProcymidone, Iprodione, and Vinclozolin; benzanilide compounds such asFlutolanil, Mepronil, and Zoxamide; piperazine compounds such asTriforine; pyrizine compounds such as Pyrifenox; carbinol compounds suchas Fenarimol; and Flutriafol; piperidine compounds such as Fenpropidine;morpholine compounds such as Fenpropimorph; organotin compounds such asFentin Hydroxide, and Fentin Acetate; urea compounds such as Pencycuron;cinnamic acid compounds such as Dimethomorph; phenylcarbamate compoundssuch as Diethofencarb; cyanopyrrole compounds such as Fludioxonil, andFenpiclonil; Strobilurin compounds such as Azoxystrobin,Kresoxim-Methyl, Metominofen, Trifloxystrobin, and Picoxystrobin;oxazolidinedione compounds such as Famoxadone; thiazole carboxamidecompounds such as Ethaboxam; silyl amide compounds such as Silthiopham;aminoacid amidecarbamate compounds such as Iprovalicarb; imidazolidinecompound such as Fenamidone; hydroxyanilide compounds such asFenhexamid; benzene sulfonamide compounds such as Flusulfamide;Strobilurin compounds such as Pyraclostrobin; anthraquinone compounds;crotonic acid compounds; antibiotics; and other compounds, such asIsoprothiolane, Tricyclazole, Pyroquilon, Diclomezine, Pro. benazole,Quinoxyfen, Propamocarb Hydrochloride, Spiroxamine, Chloropicrin,Dazomet, and Metam-Sodium.

Further, agricultural chemicals which may be used in admixture with orin combination with the compounds of the present invention, may, forexample, be the active ingredient compounds in the herbicides asdisclosed in Farm Chemicals Handbook (1998 edition), particularly thoseof soil treatment type.

Further, pesticides containing the compounds of the present inventionare useful as agents for controlling parasites on animals, particularlyas agents for controlling parasites in the bodies of animals, or asagents for controlling animal diseases caused by such parasites.

For example, they are effective for controlling (1) parasites parasiticon the exterior of a host animal, such as, acarus such as mange mite,mesostigmatid mites, sarcoptic mange mite (Sarcoptes scabiei),trombiculid mites, New Zealand cattle tick (Haemaphyalis longicornis)and southern cattle tick (Boophilus microplus); fleas such as cat flea(Ctenocephalides felis), dog flea (Ctenocephalides canis), northern ratflea (Nosopsyllus fasciatus), oriental rat flea (Xenopsylla cheopis) andhuman flea (Pulex irritans); sucking lice such as short-nosed cattlelouse (Haematopinus eurysternus), horse sucking louse (Haematopinusasini), sheep lice, long-nosed cattle louse (Linognathus vituli) andhead louse (Pediculus capitis); biting lice such as dog biting louse(Trichodectes canis); blood-sucking dipterous insects such as horse fly(Tabanus trigonus), biting midges (Culicoides schultzei) and blackfly(Simulium ornatum); and (2) parasites parasitic in the body of a hostanimal, such as, nematodes such as lung worms, whipworm (Trichuristrichiura), tuberous worm, gastric parasites, ascaris and filarioidea;tapeworms; flukes; and protozoa such as coccidia, malarial parasite(Plasmodium malariae), intestinal sarcocyst, Toxoplasma andcryptosporidium.

The compound of the present invention is usually formulated togetherwith a suitable vehicle into a formulation such as a powder, a granule,a parvule, a tablet, a dusting powder, a capsule, a solution or anemulsion. The suitable vehicle may be one which is commonly used as afeed additive, and it may, for example, be lactose, sucrose, glucose,starch, wheat powder, corn powder, soybean meal, degreased rice bran,calcium carbonate or other commercially available feed material.Further, the compound of the present invention can be used, togetherwith a vehicle, in combination with various vitamins, minerals, aminoacids, enzyme drugs, antifebriles, sedatives, antiphlogistics,bactericides, colorants, aromatizing agents, preservatives, etc. Thedose of the compound of the present invention varies depending upon theparasites as the object of control, the administration method, thepurpose of administration, the diseased degree, etc. However, it isusually administered as mixed in a feed in a concentration of at least0.1 ppm.

The compound of the present invention exhibits an effect for controllingparasites on animals, such as fleas, coccidia and filarioidea, by a testin accordance with the test method disclosed in e.g. JP-A-5-70350 orJP-A-11-500439.

Preferred embodiments in the present invention are as follows. However,it should be understood that the present invention is by no meansrestricted to such specific embodiments.

(1) An acid amide derivative of the above formula (I) or a salt thereof,wherein A is phenyl which may be substituted by X′; benzyl which may besubstituted by X, naphthyl which may be substituted by X, a heterocyclicgroup which may be substituted by X, a fused heterocyclic group whichmay be substituted by X, indanyl (the indanyl may be substituted byhalogen, alkyl or alkoxy) or tetrahydronaphthyl (the tetrahydronaphthylmay be substituted by halogen, alkyl or alkoxy), X′ is alkoxyalkoxy,haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, phenyl whichmay be substituted by Y′, phenoxy which may be substituted by Y′,benzyloxy which may be substituted by Y′, pyridyloxy which may besubstituted by Y′, —OR₄, —SR₅, —NR₆R₇, —CO₂R₈, —C(═O)NR₉R₁₀ or anunsaturated heterocyclic group (the unsaturated heterocyclic ring may besubstituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), Y′ is—OR₄, —CO₂R₁₁, —CONR₁₂R₁₃ or an unsaturated heterocyclic group (theunsaturated heterocyclic ring may be substituted by halogen, alkyl,haloalkyl, alkoxy or haloalkoxy).

(2) The acid amide derivative or a salt thereof according to the above(1), wherein A is phenyl which may be substituted by X′.

(3) The acid amide derivative or a salt thereof according to the above(1), wherein A is benzyl which may be substituted by X, naphthyl whichmay be substituted by X, a heterocyclic group which may be substitutedby X, a fused heterocyclic group which may be substituted by X, indanyl(the indanyl may be substituted by halogen, alkyl or alkoxy), ortetrahydronaphthyl (the tetrahydronaphthyl may be substituted byhalogen, alkyl or alkoxy).

(4) The acid amide derivative or a salt thereof according to the above(3), wherein A is benzyl which may be substituted by X, naphthyl whichmay be substituted by X.

(5) The acid amide derivative or a salt thereof according to the above(3), wherein A is a heterocyclic group which may be substituted by X, ora fused heterocyclic group which may be substituted by X.

(6) The acid amide derivative or a salt thereof according to the above(5), wherein the heterocyclic group is a 5- or 6-membered heterocyclicgroup containing from 1 to 4 atoms of at least one type selected fromthe group consisting of O, S and N, and the fused heterocyclic group isa 8- to 10-membered fused heterocyclic group containing from 1 to 4atoms of at least one type selected from the group consisting of O, Sand N.

(7) The acid amide derivative or a salt thereof according to the above(6), wherein the heterocyclic group is furyl, tetrahydrofuryl, thienyl,pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, imidazolyl, imidazolinyl, imidazolidinyl,pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl,thiadiazolyl, tetrazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl,oxazinyl, morpholinyl, thiazinyl, pyridazinyl, pyrimidinyl, pyrazinyl,piperazinyl or triazinyl, and the fused heterocyclic group isbenzofuranyl, isobenzofuranyl, dihydrobenzofuranyl,dihydroisobenzofuranyl, benzothienyl, isobenzothienyl,dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl,indolyl, isoindolyl, benzoxazolyl, benzothiazolyl, indazolyl,benzimidazolyl, benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl,isochromanyl, chromonyl, chromanonyl, quinolyl, isoquinolyl, cinnolinyl,phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl,imidazopyridyl, naphthyridinyl, pteridinyl, dihydrobenzoxazinyl,dihydrobenzoxazolinonyl, dihydrobenzoxazinonyl or benzothioxanyl.

(8) The acid amide derivative or a salt thereof according to the (3),wherein A is indanyl (the indanyl may be substituted by halogen, alkylor alkoxy), or tetrahydronaphthyl (the tetrahydronaphthyl may besubstituted by halogen, alkyl or alkoxy).

(9) The acid amide derivative or a salt thereof according to the above(1) or (3) to (7), wherein X is at least one type selected from thegroup consisting of halogen, alkyl, haloalkyl, alkoxy or haloalkoxy.

(10) The acid amide derivative or a salt thereof according to the above(1) to (8), wherein B is phenyl which may be substituted by Y.

(11) The acid amide derivative or a salt thereof according to the above(1) to (8), wherein each of R₁ and R₂ is alkyl, R₃ is a hydrogen atom.

(12) The acid amide derivative or a salt thereof according to the above(1) to (8), wherein B is phenyl which may be substituted by Y, each ofR₁ and R₂ is alkyl, and R₃ is a hydrogen atom.

(13) The acid amide derivative or a salt thereof according to the above(10) or (12), wherein Y is at least one type selected from the groupconsisting of halogen, alkyl or haloalkyl.

Further, other preferred embodiments in the present invention are asfollows. However, the present invention is not limited to them.

An acid amid derivative of the above formula (I) or a salt thereof,wherein A is phenyl which may be substituted by X, benzyl which may besubstituted by X, naphthyl which may be substituted by X, a heterocyclicgroup which may be substituted by X, or a fused heterocyclic group whichmay be substituted by X, B is alkyl, cycloalkyl, phenyl which may besubstituted by Y, a heterocyclic group which may be substituted by Y, ora fused heterocyclic group which may be substituted by Y, X is halogen,alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy,haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy,alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio,haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which maybe substituted by Y, phenoxy which may be substituted by Y, benzyloxywhich may be substituted by Y, pyridyloxy which may be substituted by Y,—OR₄, —SR₅, —NR₆R₇, —CO₂R₈, —C(═O)NR₉R₁₀ or an unsaturated heterocyclicgroup (the unsaturated heterocyclic ring may be substituted by halogen,alkyl, haloalkyl, alkoxy or haloalkoxy), Y is halogen, alkyl, haloalkyl,alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl,haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, —CO₂R₁₁, —CONR₁₂R₁₃ or anunsaturated heterocyclic group (the unsaturated heterocyclic ring may besubstituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each ofR₁ and R₂ is alkyl, cyano or —CO₂R₁₄, or R₁ and R₂ may together form a3- to 6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl, —COR₁₅, —S(O)mR₁₆ or —S(O)nNR₁₇R₁₈, each ofR₄ and R₆ is hydrogen, —C(═W)R₁₉, —C(═W)OR₂₀, —C(═W)SR₂₁, —C(═W)NR₂₂R₂₃,—S(O)qR₂₄ or —S(O)rNR₂₅R₂₆, R₅ is hydrogen, —C(═W)R₁₉, —C(═W)OR₂₀,—C(═W)SR₂₁ or —C(═W)NR₂₂R₂₃, R₇ is hydrogen, alkyl or haloalkyl, each ofR₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃ and R₁₄ is hydrogen or alkyl, R₁₅ ishydrogen, alkyl or alkoxy, each of R₁₆, R₁₇, R₁₈, R₁₉, R₂₀, R₂₁, R₂₂,R₂₃, R₂₄ , R₂₅ and R₂₆ is alkyl, haloalkyl or phenyl (the phenyl whichmay be substituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy),each of m, n, q and r is from 0 to 2, W is oxygen or sulfur.

Now, Examples of the present invention will be described. However, itshould be understood that the present invention is by no meansrestricted to such specific Examples. Firstly, Preparation Examples forthe compounds of the present invention will be described.

PREPARATION EXAMPLE 1

Preparation of2-hydroxycarbonyl-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide (Theafter-mentioned Compound No. 1-120)

0.83 g of triethylamine was added to a mixture comprising 1.92 g ofα-amino-4-chloroisobutyrophenone hydrochloride and 20 ml oftetrahydrofuran at room temperature, and a mixed solution of 1.21 g ofphthalic anhydride and 30 ml of tetrahydrofuran was added thereto,followed by a reaction at room temperature for 16 hours. Aftercompletion of the reaction, the reaction mixture was concentrated, and70 ml of water was added to the residue, followed by acidification by10% hydrochloric acid, and then by stirring for 30 minutes. Theprecipitated crystal was collected by filtration, washed with water,dissolved in ethyl acetate, and then dried over anhydrous magnesiumsulfate, followed by concentration under reduced pressure to obtain 1.84g of the desired product having a melting point of from 212 to 214° C.The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: DMSO/400 MHz) 1.53(s, 6H),7.00(d, 1H),7.48(t,1H),7.52-7.55(m, 3H),7.75(d, 1H),8.05(d, 2H),9.11(s, 1H),12.96(brs, 1H).

PREPARATION EXAMPLE 2

Preparation of2-(3-thienyl)-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide (Theafter-mentioned Compound No. 1-80)

0.24 g of 3-thiopheneboric acid, 0.51 g of sodium carbonate, 5 ml ofwater and 0.1 g of tetrakis(triphenylphosphine)palladium(0) were addedto a mixed solution comprising 0.35 g of2-bromo-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide and 5 ml of1,2-dimethoxyethane, followed by a reaction under heating and refluxingfor 8 hours under nitrogen atmosphere. After completion of the reaction,the reaction mixture was allowed to cool and added to 40 ml of water,then 20 ml of t-butyl methyl ether was added and stirred, followed byneutralization with 30% sulfuric acid, and then by extraction with ethylacetate. The organic layer was washed with an aqueous sodium chloridesolution, then dried over anhydrous sodium sulfate, followed byconcentration under reduced pressure. The obtained residue was purifiedby silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/7)to obtain 0.14 g of the desired product having a melting point of from170 to 173° C. The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.48(s, 6H),6.09(brs, 1H),7.13(dd,1H),7.32-7.48(m, 8H), 7.84(dd, 2H).

PREPARATION EXAMPLE 3

Preparation of 2,6-difluoro-N-[1-methyl-l-(3-thenoyl)ethyl]benzamide(The after-mentioned Compound No. 6-5)

(1) 2.88 g of phenyltrimethylammonium tribromide was added to a mixedsolution comprising 1.54 g of 2-(3-thenoyl)propane and 30 ml oftetrahydrofuran, followed by a reaction at room temperature for 15hours. After completion of the reaction, the precipitate was separatedby filtration and concentrated, and then purified by silica gel columnchromatography (eluent: ethyl acetate/n-hexane=2/8-4/6) to obtain 0.87of 2-bromo-2-(3-thenoyl)propane. The NMR spectrum data of this productwere as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 2.06(s, 6H),7.27-7.31(m,1H),7.74(dd, 1H),8.40(dd, 1H).

(2) 0.87 of 2-bromo-2-(3-thenoyl)propane was dissolved in 5 ml ofdimethyl sulfoxide, then 0.44 g of sodium azide was added thereto andreacted at 70° C. for 1 hour. After completion of the reaction, thereaction mixture was allowed to cool and put into 200 ml of water, andthen extracted with ethyl ether. The organic layer was washed withwater, then dried over magnesium sulfate, followed by concentration toobtain 0.70 g of 2-azido-2-(3-thenoyl)propane. The NMR spectrum data ofthis product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.58(s, 6H),7.27-7.32(m,1H),7.69(dd, 1H),8.45(dd, 1H).

(3) 4 ml of tetrahydrofuran and 0.08 ml of water were added to 0.68 g of2-azido-2-(3-thenoyl)propane, then 1.10 g of triphenylphosphine wasgradually added thereto with stirring at room temperature, and aftercompletion of addition, a reaction was carried out for 18 hours. 15 mlof tetrahydrofuran was added to the reaction mixture, then 0.30 g oftriethylamine was added, followed by cooling with ice, and a mixedsolution of 0.46 g of 2,6-difluorobenzoyl chloride and 5 ml oftetrahydrofuran was dropwise added thereto. After completion of thedropwise addition, a reaction was carried out for 30 minutes undercooling with ice, and then a further reaction was carried out for 2.5hours at room temperature. After completion of the reaction, thereaction mixture was put into 100 ml of water and extracted by ethylacetate. The organic layer was dried over sodium sulfate, concentratedand purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=4/6) to obtain 0.60 g of the desired product having amelting point of from 139 to 142° C. The NMR spectrum data of thisproduct were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.81(s, 6H),6.92(t, 2H),7.12(br,1H),7.29-7.38(m, 2H), 7.66(dd, 1H),8.24(dd, 1H).

PREPARATION EXAMPLE 4

Preparation of2,6-difluoro-N-[(1,1-dimethyl-4′-methylsulfonyloxy)phenacyl]benzamide(Compond No. 1-25)

(1) 0.85 g of phenyltrimethylammonium tribromide was added to a mixturecomprising 0.55 g of 4-methylsulfonyloxy isobutyrophenone and 10 ml oftetrahydrofuran, followed by a reaction at room temperature for 6 hours.After completion of the reaction, the reaction mixture was subjected tofiltration, and the filtrate was concentrated under reduced pressure toobtain 0.68 g of oily α-bromo-4-methylsulfonyloxyisobutyrophenone. TheNMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 2.04(s, 6H),3.24(s, 3H),7.35(d,2H),8.23(d, 2H)

(2) 0.28 g of sodium azide was added to a mixture comprising 0.68 g ofa-bromo-4-methylsulfonyloxyisobutyrophenone and 4 ml of dimethylsulfoxide, followed by a reaction at 50° C. for 3 hours. Aftercompletion of the reaction, the reaction mixture was put into water andthen extracted with ethyl ether, followed by washing with water. Theorganic layer was dried over anhydrous magnesium sulfate, followed byconcentration under reduced pressure to obtain 0.55 g ofα-azido-4-methylsulfonyloxyisobutyrophenone. The NMR spectrum data ofthis product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.61(s, 6H),3.20(s, 3H),7.39(d,2H),8.21(d, 2H)

(3) 0.61 g of triphenylphosphine was added to a mixture comprising 0.55g of α-azido-4-methylsulfonyloxyisobutyrophenone, 12.7 ml oftetrahydrofuran and 0.3 ml of water, followed by a reaction at roomtemperature for 16 hours. After completion of the reaction, the reactionmixture was concentrated under reduced pressure, and the residue wasweakly acidified by adding water and then hydrochloric acid, and thenwashed with ethyl acetate. The aqueous layer was neutralized with anaqueous NaOH solution and extracted with methylene chloride, followed bydrying over anhydrous sodium sulfate and concentration under reducedpressure to obtain 0.40 g of oilyα-amino-4-methylsulfonyloxyisobutyrophenone.

(4) 0.19 g of triethylamine was added to a mixture comprising 0.40 g ofα-amino-4-methylsulfonyloxyisobutyrophenone and 15 ml oftetrahydrofuran, and then 0.27 g of 2,6-difluorobenzoyl chloride wasdropwise added thereto under cooling with ice. After completion of thedropwise addition, the mixture was reacted at room temperature for 2hours. After completion of the reaction, the reaction mixture was washedwith water and dried over anhydrous sodium sulfate, followed byconcentration under reduced pressure. The obtained residue was purifiedby silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/7)to obtain 0.50 g of the desired product having a melting point of from158 to 162° C. The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.78(s, 6H),3.15(s, 3H),6.89(s,1H),6.91(t, 2H),7.32(d, 2H), 7.32-7.42(m, 1H),8.09(d, 2H).

PREPARATION EXAMPLE 5

Preparation of2,6-difluoro-N-[(1,1-dimethyl-4′-hydroxy)phenacyl]benzamide (CompoundNo. 1-2)

At room temperature, a mixture comprising 0.3 g of sodium hydroxide and15 ml of water was added to a mixture comprising 0.49 g of2,6-difluoro-N-[(1,1-dimethyl-4′-methylsufonyloxy)phenacyl]benzamide and30 ml of methanol, followed by a reaction under refluxing for 1 hour.After completion of the reaction, the reaction mixture was concentratedunder reduced pressure, then the residue was diluted with water andweakly acidified with hydrochloric acid, and then the precipitated solidwas collected by filtration, followed by drying to obtain 0.35 g of thedesired product having a melting point of from 107 to 114° C. The NMRspectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.86(s, 6H),6.77(s, 1H),6.83(d,2H),6.93(t, 2H),7.06(s, 1H), 7.30-7.40(m, 1H),8.02(d, 2H)

PREPARATION EXAMPLE 6

Preparation of2,6-difluoro-N-[(1,1-dimethyl-4′-trifluoromethylsulfonyloxy)phenacyl]benzamide(Compound No. 1-26)

0.102 g of trifluoromethanesulfonate anhydride was added to a mixturecomprising 0.115 g of2,6-difluoro-N-[(1,1-dimethyl-4′-hydroxy)phenacyl]benzamide, 7 ml ofdichloroethane and 44 mg of triethylamine under cooling with ice,followed by a reaction at room temperature for 2 hours. After completionof the reaction, the reaction mixture was diluted with methylenechloride and washed with water, and then dried over anhydrous sodiumsulfate, followed by concentration under reduced pressure. The obtainedresidue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=3/7) to obtain 0.14 g of the desired product having amelting point of from 117 to 123° C. The NMR spectrum data of thisproduct were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.78(s, 6H),6.60(s, 1H),6.91(t,2H),7.31(d, 2H), 7.31-7.41(m, 1H),8.10(d, 2H).

PREPARATION EXAMPLE 7

Preparation of2-methoxycarbonyl-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide (Theafter-mentioned Compound No. 1-121)

A catalytic amount of concentrated sulfuric acid was added at roomtemperature to a mixed solution comprising 1.4 g of2-hydroxycarbonyl-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide and 100ml of methanol, and the mixture was reacted under heating refluxing for6 hours. After completion of the reaction, the methanol was distilledoff and then 150 ml of water was added to the residue, followed byextraction with ethyl acetate. The organic layer was dried overanhydrous magnesium sulfate, followed by concentration under reducedpressure. The obtained residue was purified by silica gel columnchromatography (eluent: ethyl acetate/n-hexane=2/8-4/6) to obtain 0.86 gof the desired product having a melting point of from 166 to 168° C. TheNMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.80(s, 6H),3.84(s, 3H),6.77(brs,1H),7.18(dd, 1H), 7.41(dd, 2H),7.43-7.51(m, 2H),7.86(dd, 1H),7.98(dd,2H).

PREPARATION EXAMPLE 8

Preparation of2-aminocarbonyl-N-[(4′-chloro-1,1-dimethyl)phenacyl]benzamide (Theafter-mentioned Compound No. 1-122)

10 ml of 28% aqueous ammonia was added at room temperature to a mixedsolution comprising 0.58 g of2-methoxycarbonyl-N-[(4′-chloro-l,1-dimethyl)phenacyl]benzamide and 15ml of methanol, and the mixture was reacted overnight at roomtemperature. After completion of the reaction, the methanol wasdistilled off, and then 200 ml of water was added to the residue,followed by neutralization with 30% sulfuric acid, then by extractionwith ethyl acetate and then by washing with a saturated sodium chlorideaqueous solution. The organic layer was dried over anhydrous magnesiumsulfate, followed by concentration under reduced pressure. The obtainedresidue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=1/1-8/2) to obtain 0.39 g of the desired product havinga melting point of from 205 to 206° C. The NMR spectrum data of thisproduct were as follows.

¹H-NMR δppm (Solvent: DMSO/400 MHz) 1.52(s, 6H),7.17-7.21(m,1H),7.34(brs, 1H),7.41-7.49(m, 3H), 7.52(dd, 2H),7.68(brs, 1H),8.05(dd,2H),9.09(s, 1H).

PREPARATION EXAMPLE 9

Preparation of2-fluoro-N-[2-[(2,2,3,3,-tetrafluoro-5-methyl-1,4-benzodioxan-6-yl)carbonyl]-2-propyl]benzamide(The after-mentioned Compound No. 16-37)

(1) Under nitrogen atmosphere, 11.7 ml of n-butyllithium (1.57M-n-hexane solution) was dropwise added at −20° C. to a mixture of 1.85g of diisopropylamine and 50 ml of tetrahydrofuran, and then the mixturewas stirred at the same temperature for 30 minutes. 5.0 g of6-bromo-2,2,3,3,-tetrafluoro-1,4-benzodioxane was dropwise added theretoat a temperature of at most −50° C., followed by stirring at the sametemperature for 30 minutes. Then, 5.5 ml of methyl iodide was dropwiseadded thereto at a temperature of at most −70° C., and then thetemperature was raised to room temperature, followed by a reaction for15 hours. After completion of the reaction, the reaction mixture was putinto water and then weakly acidified by an addition of hydrochloricacid. Then, the mixture was extracted with ethyl ether, and the extractwas washed with water and dried over magnesium sulfate, followed byconcentration under reduced pressure. The obtained residue was purifiedby silica gel column chromatography (eluent: n-hexane) to obtain 3.40 gof oily 6-bromo-2,2,3,3,-tetrafluoro-5-methyl-1,4-benzodioxane. The NMRspectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDC13/400 MHz) 2.39(s, 3H),6.89(d, 1H),6.91(t,2H),7.35(d, 1H).

(2) Under nitrogen atmosphere, 7.8 ml of n-butyllithium (1.57 M-n-hexanesolution) was dropwise added at −50° C. to a mixture comprising 3.36 gof 6-bromo-5 2,2,3,3,-tetrafluoro-5-methyl-1,4-benzodioxane and 40.6 mlof ethyl ether, and then the mixture was stirred at the same temperaturefor 30 minutes. 0.89 g of isobutylaldehyde was dropwise added thereto ata temperature of at most −70 ° C., and the temperature was raised toroom temperature followed by a reaction for 15 hours. After completionof the reaction, the reaction mixture was put into water, and thenweakly acidified by an addition of hydrochloric acid. Then the mixturewas extracted with ether, and the extract was washed with water anddryied over magnesium sulfate, followed by concentration under reducedpressure. The obtained residue was purified by silica gel columnchromatography (eluent: ethyl acetate/n-hexane=1/9) to obtain 1.90 g ofoily1-(2,2,3,3,-tetrafluoro-5-methyl-1,4-benzodioxan-6-yl)-2-methylpropanol.The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 0.87(d, 3H),1.00(d, 3H),1.94(m,1H),2.29(s, 3H),4.65(d, 1H), 7.00(d, 1H),7.27(d, 1H).

(3) At room temperature, a mixture of 1.82 g of1-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxan-6-yl)-2-methylpropanoland 7 ml of methylene chloride was added to a mixture of 2.0 g ofpyridinium chlorochromate, 1.01 g of sodium acetate and 20 ml ofmethylene chloride, followed by a reaction at the same temperature for 2hours. After completion of the reaction, the reaction mixture wasfiltrated by cerite, and the filtrate was concentrated under reducedpressure. The obtained residue was purified by silica gel columnchromatography (eluent: ethyl acetate/n-hexane=1/19) to obtain 1.70 g ofoily 6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl) 2-propyl ketone.The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.17(d, 6H),2.36(s, 3H),3.26(m,1H),7.04(d, 1H),7.31(d, 1H).

(4) 2.15 g of phenyltrimethylammonium tribromide was added to a mixturecomprising 1.67 g of 6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl)2-propyl ketone and 20 ml of tetrahydrofuran, followed by a reaction atroom temperature for 2 hours. After completion of the reaction, thereaction mixture was filtrated, and the filtrate was concentrated underreduced pressure to obtain 1.90 g of oily6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl) 2-bromo-2-propylketone.

(5) 0.74 g of sodium azide was added to a mixture comprising 1.90 g of6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl) 2-bromo-2-propylketone and 11 ml of dimethyl sulfoxide, followed by a reaction at 50° C.for 2 hours. After completion of the reaction, the reaction mixture wasput into water and extracted with ethyl ether, and then washed withwater. The organic layer was dried over anhydrous magnesium sulfate,followed by concentration under reduced pressure. The obtained residuewas purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=1/19) to obtain 0.90 g of the oily6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl) 2-azido-2-propylketone. The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.56(s, 6H),2.25(s, 3H),7.03(d,1H),7.27(d, 1H).

(6) A mixture comprising 0.90 g of6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl) 2-azido-2-propylketone, 20 ml of methanol and 50 mg of 5% palladium-carbon, was reactedat room temperature for 1 hour under hydrogen atmosphere. Aftercompletion of the reaction, the reaction mixture was filtrated bycerite, and then the filtrate was concentrated under reduced pressure,to obtain 0.70 g of oily6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl) 2-amino-2-propylketone.

(7) 0.10 g of triethylamine was added to a mixture comprising 0.20 g of6-(2,2,3,3-tetrafluoro-5-methyl-1,4-benzodioxanyl) 2-amino-2-propylketone and 7 ml of tetrahydrofuran. 0.11 g of 2-fluorobenzoyl chloridewas dropwise added thereto under cooling with ice. After completion ofthe dropwise addition, a reaction was carried out at room temperaturefor 2 hours. After completion of the reaction, the reaction mixture waswashed with water, and then dried over anhydrous sodium sulfate,followed by concentration under reduced pressure. The obtained residuewas purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=3/7) to obtain 0.25 g of the desired product having amelting point of from 110 to 112° C. The NMR spectrum data of thisproduct were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.74(s, 6H),2.35(s, 3H),6.94(d,1H),7.14(dq, 1H), 7.23(dt, 1H),7.30(s, 1H),7.42(d, 1H), 7.44-7.50(m,1H),7.92(dt, 1H)

PREPARATION EXAMPLE 10

Preparation of2,6-difluoro-N-[(3′-methoxycarbonyl-1,1-dimethyl)phenacyl]benzamide (Theafter-mentioned Compound No. 1-221)

(1) A mixture comprising 2.48 g of m-iodobenzoic acid and 40 ml oftetrahydrofuran was cooled to −70° C., then 13.8 ml of n-butyllithium(1.6 M-n-hexane solution) was dropwise added over a period of 10minutes, followed by stirring at the same temperature for 30 minutes.Then, a mixture comprising 1.5 g of N-isobutyrylpropyleneimine and 5 mlof tetrahydrofuran was added thereto at −70° C., and then thetemperature was raised to room temperature, and a reaction was carriedout overnight.

After completion of the reaction, the reaction mixture was added to 100ml of water and stirred, and then hexane was added thereto, followed byliquid separation. The aqueous layer was acidified by concentratedhydrochloric acid and then extracted with ethyl acetate. The extract wasdried over anhydrous sodium sulfate, followed by concentration underreduced pressure to obtain a crude product of m-isobutyrylbenzoic acid.

(2) 100 ml of toluene and 5 g of thionyl chloride were added to thecrude product of m-isobutyrylbenzoic acid obtained in the above step(1), and the mixture was reacted under refluxing for 1 hour. Aftercompletion of the reaction, excess thionyl chloride was distilled off toobtain a toluene solution of crude m-isobutyrylbenzoic acid chloride.

(3) The toluene solution of crude m-isobutyrylbenzoic acid chlorideobtained in the above step (2) was dropwise added under cooing with iceto a mixture comprising 5 g of triethylamine and 100 ml of methanol, andthe mixture was heated to room temperature and reacted for 1 hour. Aftercompletion of the reaction, methanol and toluene were distilled offunder reduced pressure. Then, 200 ml of water was added thereto,followed by extraction with ethyl acetate, and then the extract wasdried over anhydrous sodium sulfate, followed by concentration underreduced pressure to obtain 1.5 g of a crude product of methylm-isobutyrylbenzoate.

(4) 0.8 g of phenyltrimethylammonium tribromide was added to a mixturecomprising 1.5 g of the crude product of methyl m-isobutyrylbenzoateobtained in the above step (3) and 20 ml of tetrahydrofuran, andfollowed by a reaction at room temperature overnight. After completionof the reaction, the precipitated crystal was separated by filtration,then tetrahydrofuran was distilled off. The residue was dissolved inethyl acetate, then washed with a saturated sodium chloride aqueoussolution, followed by drying over anhydrous sodium sulfate. Then,concentration under reduced pressure was carried out, and then, roughpurification was carried out by silica gel column chromatography toobtain 0.27 g of crude 3′-methoxycarbonyl-2-bromo-2-methylpropiophenone.The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 2.05(s, 6H),3.98(s,3H),7.52-7.57(m, 1H),8.19-8.25(m, 1H), 8.31-8.34(m, 1H),8.78(t, 1H).

(5) 17 mg of a crude product containing the desired product was obtainedby employing 0.27 g of the crude3′-methoxycarbonyl-2-bromo-2-methylpropiophenone obtained in the abovestep (4), in accordance with the steps (5) to (7) in Preparation Example9. The NMR spectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.81(s, 6H),3.93(s,3H),6.85-6.91(m, 3H),7.27-7.34(m, 1H), 7.47-7.53(m, 1H),8.16-8.20(m,2H),8.65(t, 1H).

PREPARATION EXAMPLE 11

Preparation of2,6-difluoro-N-[2-(5-trifluoromethyl-2-pyridylcarbonyl)-2-propyl]benzamide(The after-mentioned Compound No. 8-43)

10 mg of a crude product containing the desired product was obtained byemploying 2.26 g of 2-bromo-5-trifluoromethylpyridine, in accordancewith the steps (1), (4) and (5) in Preparation Example 10. The NMRspectrum data of this product were as follows.

¹H-NMR δppm (Solvent: CDCl₃/400 MHz) 1.89(s, 6H),6.71(br,1H),6.83-6.88(m, 2H),7.26-7.36(m, 1H), 10 8.04-8.11(m, 1H),8.76(s, 1H).

Now, typical examples of the compound of the present invention of theabove formula (I) will be given in Tables 1 to 53. These compounds canbe prepared in accordance with the above Preparation Examples or by theabove-described various processes for the production of the compounds ofthe present invention.

In the table, Me indicates a methyl group, Et an ethyl group, Bu a butylgroup, and Ph a phenyl group. Further, Ph(2-F) indicates that a fluorineatom is substituted at the 2-position. The same applies to otherexpressions.

TABLE 1

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 1-1 Me Me H 4-OHPh(2-F) 1-2 Me Me H 4-OH Ph(2,6-F₂) 107-114 1-3 Me Me H 4-OH Ph(2-Cl)1-4 Me Me H 4-OH Ph(2-CF₃) 1-5 Me Me H 4-OCOMe Ph(2-F) 1-6 Me Me H4-OCOMe Ph(2,6-F₂) 1-7 Me Me H 4-OCOCF₃ Ph(2-F) 1-8 Me Me H 4-OCOCF₃Ph(2,6-F₂) 1-9 Me Me H 4-OCO₂Me Ph(2-F) 1-10 Me Me H 4-OCO₂Me Ph(2,6-F₂)46-51 1-11 Me Me H 4-OCONMe₂ Ph(2-F) 1-12 Me Me H 4-OCONMe₂ Ph(2,6-F₂)136-142 1-13 Me Me H 4-OCOSPh Ph(2-F) 1-14 Me Me H 4-OCOSMe Ph(2,6-F₂)82-88 1-15 Me Me H 4-OCOSMe Ph(2-F) 1-16 Me Me H 4-OCSOMe Ph(2,6-F₂)1-17 Me Me H 4-OCS₂Me Ph(2-F) 1-18 Me Me H 4-OCS₂Me Ph(2,6-F₂) 1-19 MeMe H 4-OCSNMe₂ Ph(2-F) 1-20 Me Me H 4-OCSNMe₂ Ph(2,6-F₂) 1-21 Me Me H4-OCS₂Me Ph(2-F) 1-22 Me Me Na 4-OCS₂Me Ph(2,6-F₂) 1-23 Me Me H 4-OSCCl₃Ph(2-F) 1-24 Me Me H 4-OSOMe Ph(2,6-F₂) 1-25 Me Me H 4-OSO₂Me Ph(2,6-F₂)158-162 1-26 Me Me H 4-OSO₂CF₃ Ph(2,6-F₂) 117-123 1-27 Me Me H 4-OSO₂PhPh(2-F) 1-28 Me Me H 4-OSO₂Ph Ph(2,6-F₂) 1-29 Me Me H 4-OSNMe₂Ph(2,6-F₂) 1-30 Me Me H 4-OSO₂NMe₂ Ph(2-F) 1-31 Me Me H 4-OSO₂NMe₂Ph(2,6-F₂) Oil 1-32 Me Me H 4-NH₂ Ph(2-F) 1-33 Me Me H 4-NH₂ Ph(2,6-F₂)170-180 1-34 Me Me H 4-NH₂.HCl Ph(2,6-F₂) 142-155 1-35 Me Me H 4-NHCOMePh(2-F) 1-36 Me Me H 4- Ph(2,6-F₂) 275-281 NHCOBu(t) 1-37 Me Me H4-NHCOCF₃ Ph(2-F) 1-38 Me Me H 4-NHCOCF₃ Ph(2,6-F₂) 1-39 Me Me H4-NHCO₂Me Ph(2-F) 1-40 Me Me H 4-NHCO₂Me Ph(2,6-F₂) 1-41 Me Me H 4-Ph(2-F) N(Me)CO₂Me 1-42 Me Me H 4-NHCONMe₂ Ph(2,6-F₂) 1-43 Me Me H4-NHCOSMe Ph(2-F) 1-44 Me Me H 4-NHCOSMe Ph(2,6-F₂) 1-45 Me Me H4-NHCSOMe Ph(2-F) 1-46 Me Me H 4-NHCSOMe Ph(2,6-F₂) 1-47 Me Me H4-NHCS₂Me Ph(2-F) 1-48 Me Me H 4-NHCS₂Me Ph(2,6-F₂) 1-49 Me Me H4-NHCSNMe₂ Ph(2-F) 1-50 Me Me H 4-NHCSNMe₂ Ph(2,6-F₂) 1-51 Me Me H4-NHCS₂Ph Ph(2-F) 1-52 Me Me H 4-NHCS₂Ph Ph(2,6-F₂) 1-53 Me Me H4-NHSCCl₃ Ph(2-F) 1-54 Me Me H 4-NHSOMe Ph(2,6-F₂) 1-55 Me Me H4-NHSO₂Me Ph(2-F) 1-56 Me Me H 4-NHSO₂Me Ph(2,6-F₂) 195-233 1-57 Me Me H4-NHSO₂Ph Ph(2-F) 1-58 Me Me H 4-NHCOPh Ph(2,6-F₂) 270-283 1-59 Me MeSCCl₃ 4-F Ph(2-F) 1-60 Me Me SCCl₃ 4-Cl Ph(2,6-F₂) 1-61 Me Me SPh 4-BrPh(2-F) 1-62 Me Me SPh 4-F Ph(2,6-F₂) 1-63 Me Me SOPh 4-Cl Ph(2,6-F₂)1-64 Me Me SO₂Me 4-Br Ph(2-F) 1-65 Me Me SO₂Me 4-F Ph(2,6-F₂) 1-66 Me MeSO₂Ph 4-Cl Ph(2-F) 1-67 Me Me SO₂Ph 4-Br Ph(2,6-F₂) 1-68 Me Me SO₂NMe₂4-F Ph(2-F) 1-69 Me Me SO₂NMe₂ 4-Cl Ph(2,6-F₂) 1-70 Me Me SO₂CF₃ 4-BrPh(2-F) 1-71 Me Me SO₂CF₃ 4-F Ph(2,6-F₂) 1-72 Me Me H 4-CO₂H Ph(2,6-F₂)215-218 1-73 Me Me H 4-CO₂Me Ph(2,6-F₂) 58-60 1-74 Me Me H 4-CO₂EtPh(2,6-F₂) 1-75 Me Me H 4-CONH₂ Ph(2,6-F₂) >250 1-76 Me Me H 4-CONHMePh(2,6-F₂) 244-259 1-77 Me Me H 4-CONMe₂ Ph(2,6-F₂) 158-160 1-78 Me Me H4-Cl Ph(2-CO₂H) 212-214 1-79 Me Me H 4-Cl Ph(2-(2-thienyl)) 1-80 Me Me H4-Cl Ph(2-(3-thienyl)) 170-173 1-81 Me Me H 4-Cl Ph(2-(2-pyridyl)) 1-82Me Me H 4-Cl Ph(2-(3-pyridyl)) 1-83 Me Me H 4-Cl Ph(2-(4-pyridyl)) 1-84Me Me H 4-Br Ph(2-CO₂H) 197-199 1-85 Me Me H 4-Br Ph(2-(2-thienyl)) 1-86Me Me H 4-Br Ph(2-(3-thienyl)) 1-87 Me Me H 4-Br Ph(2-(2-pyridyl)) 1-88Me Me H 4-Br Ph(2-(3-pyridyl)) 1-89 Me Me H 4-Br Ph(2-(4-pyridyl)) 1-90Me Me H 4-(2-pyridyl) Ph(2,6-F₂) 1-91 Me Me H 4-(3-pyridyl) Ph(2,6-F₂)1-92 Me Me H 4-(4-pyridyl) Ph(2,6-F₂) 1-93 Me Me H 4-(2-thienyl) Ph(2-F)110-112 1-94 Me Me H 4-(3-thienyl) Ph(2-F) 143-145 1-95 Me Me H4-(2-thienyl) Ph(2,6-F₂) 1-96 Me Me H 4-(3-thienyl) Ph(2,6-F₂) 1-97 MeMe H 4-Cl Ph(2-CO₂Me) 1-98 Me Me H H Ph(2-CO₂Me) 1-99 Me CO₂Et H HPh(2-F) 122-123 1-100 Me CO₂Et H H Ph(2.6-F₂) 117-119 1-101 Me CN H HPh(2-F) Oil 1-102 Me CN H H Ph(2,6-F₂) 45-48 1-103 Me Me H 4-Br1-naphthyl 1-104 Me Me H 4-Br 2-naphthyl 1-105 Me Me H 4-Br 2-thienyl235-240 1-106 Me Me H 4-Br 3-thienyl 245-247 1-107 Me Me H 4-Br2-pyrazinyl 122-125 1-108 Me Me H 4-Br 2-quinolyl 1-109 Me Me H 4-Br3-quinolyl 192-195 1-110 Me Me H 4-Br Indol-2-yl 1-111 Me Me H 4-BrIndol-3-yl 1-112 Me Me H 4-Br 3-furyl 1-113 Me Me H 4-Br 2,5-dimethyl-3-183-185 furyl 1-114 Me Me H 4-Br 2-furyl 1-115 Me Me H 4-Br5-nitro-2-furyl 132-134 1-116 Me Me H 4-Br Benzofuran-2-yl 164-166 1-117Me Me H 4-Br 2,3- 145-147 dihydrobenzofuran- 2-yl 1-118 Me Me H 4-Br1,4-benzodioxane- 45-47 2-yl 1-119 Me Me H 4-Br N-methylindol-2-yl 50-581-120 Me Me H 4-Cl Ph(2-CO₂H) 212-214 1-121 Me Me H 4-Cl Ph(2-CO₂Me)166-168 1-122 Me Me H 4-Cl Ph(2-CONH₂) 205-206 1-123 Me Me H 4-OSO₂MePh(2-F) 130-133 1-124 Me Me H 4-OSO₂Me Ph(2-Cl) 1-125 Me Me H 4-OSO₂CF₃Ph(2-F) 72-75 1-126 Me Me H 4-OSO₂CF₃ Ph(2-Cl) 1-127 Me Me H 4-SCH₂CF₃Ph(2,6-F₂) 110-112 1-128 Me Me H 4-SCH₂CF₃ Ph(2-F) Oil 1-129 Me Me H4-SCH₂CF₃ Ph(2-Cl) 1-130 Me Me H 4-SCHF₂ Ph(2,6-F₂) 108-110 1-131 Me MeH 4-SCHF₂ Ph(2-F) 77-79 1-132 Me Me H 4-SCHF₂ Ph(2-Cl) 1-133 Me Me H4-SO₂CH₂CF₃ Ph(2,6-F₂) 175-178 1-134 Me Me H 4-SO₂CH₂CF₃ Ph(2-F) 135-1391-135 Me Me H 4-SO₂CH₂CF₃ Ph(2-Cl) 1-136 Me Me H 4-SO₂CHF₂ Ph(2,6-F₂)140-144 1-137 Me Me H 4-SO₂CHF₂ Ph(2-F) 85-88 1-138 Me Me H 4-SO₂CHF₂Ph(2-C1) 1-139 Me Me H 2-Me-4-OSO₂Me Ph(2,6-F₂) 112-115 1-140 Me Me H2-Me-4-OSO₂CF₃ Ph(2,6-F₂) 108-110 1-141 Me Me H 2-Me-4-OCF₂CHFOCF₃Ph(2-F) 1-142 Me Me H 2-Me-4-OCF₂CHFOCF₃ Ph(2,6-F₂) 1-143 Me Me H2-Me-4-OCF₂CHFOCF₃ Ph(2-Cl) 1-144 Me Me H 2-Me-4-OCF₂CHFOCF₃ Ph(2-Me)1-145 Me Me H 2-Me-4-OCF₂CHFOCF₃ Ph(2-CF₃) 1-146 Me Me H2-Me-4-OCF₂CHFOCF₃ Ph(2-F-6-Cl) 1-147 Me Me H 2-Cl-4-OCF₂CHFOCF₃ Ph(2-F)1-148 Me Me H 2-Cl-4-OCF₂CHFOCF₃ Ph(2,6-F₂) 1-149 Me Me H2-Cl-4-OCF₂CHFOCF₃ Ph(2-Cl) 1-150 Me Me H 2-Cl-4-OCF₂CHFOCF₃ Ph(2-Me)1-151 Me Me H 2-Cl-4-OCF₂CHFOCF₃ Ph(2-CF₃) 1-152 Me Me H2-Cl-4-OCF₂CHFOCF₃ Ph(2-F-6-Cl) 1-153 Me Me H 2,3-Me₂-4-OCF₂CHFOCF₃Ph(2-F) 1-154 Me Me H 2,3-Me₂-4-OCF₂CHFOCF₃ Ph(2,6-F₂) 1-155 Me Me H2,3-Me₂-4-OCF₂CHFOCF₃ Ph(2-Cl) 1-156 Me Me H 2,3-Me₂-4-OCF₂CHFOCF₃Ph(2-Me) 1-157 Me Me H 2,3-Me₂-4-OCF₂CHFOCF₃ Ph(2-CF₃) 1-158 Me Me H2,3-Me₂-4-OCF₂CHFOCF₃ Ph(2-F-6-Cl) 1-159 Me Me H2-Me-3-OMe-4-OCF₂CHFOCF₃ Ph(2-F) 1-160 Me Me H 2-Me-3-OMe-4-OCF₂CHFOCF₃Ph(2,6-F₂) 1-161 Me Me H 2-Me-3-OMe-4-OCF₂CHFOCF₃ Ph(2-Cl) 1-162 Me Me H2-Me-3-OMe-4-OCF₂CHFCCF₃ Ph(2-Me) 1-163 Me Me H 2-Me-3-OMe-4-OCF₂CHFOCF₃Ph(2-CF₃) 1-164 Me Me H 2-Me-3-OMe-4-OCF₂CHFOCF₃ Ph(2-F-6-Cl) 1-165 MeMe H 2-Me-3-OCHF₂-4-OCF₂CHFOCF₃ Ph(2-F) 1-166 Me Me H2-Me-3-OCHF₂-4-OCF₂CHFOCF₃ Ph(2,6-F₂) 1-167 Me Me H2-Me-3-OCHF₂-4-OCF₂CHFOCF₃ Ph(2-Cl) 1-168 Me Me H2-Me-3-OCHF₂-4-OCF₂CHFOCF₃ Ph(2-Me) 1-169 Me Me H2-Me-3-OCHF₂-4-OCF₂CHFOCF₃ Ph(2-CF₃) 1-170 Me Me H2-Me-3-OCHF₂-4-OCF₂CHFOCF₃ Ph(2-F-6-Cl) 1-171 Me Me H 4-Br Ph(2- 253-254CONHCH₂CH(Me)₂) 1-172 Me Me H 4-Br Ph(2-CONHMe) 252-255 1-173 Me Me H4-Br Ph(2-CONH₂) 193-196 1-174 Me Me H 4-Br Ph(2-OCOMe) 163-166 1-175 MeMe H 4-Br Ph(2-CO₂Me) 151-154 1-176 Me Me H 4-Cl Ph(2-CO₂Me) 166-1681-177 Me Me H 4-Cl Ph(2-CONH₂) 205-206 1-178 Me Me H 2-CO₂H Ph(2-F)1-179 Me Me H 2-CO₂H Ph(2,6-F₂) 1-180 Me Me H 2-CO₂H Ph(2-Cl) 1-181 MeMe H 2-CO₂H Ph(2-Me) 1-182 Me Me H 2-CO₂H Ph(2-CF₃) 1-183 Me Me H 2-CO₂HPh(2-F-6-Cl) 1-184 Me Me H 2-CO₂Me Ph(2-F) 1-185 Me Me H 2-CO₂MePh(2,6-F₂) 1-186 Me Me H 2-CO₂Me Ph(2-Cl) 1-187 Me Me H 2-CO₂Me Ph(2-Me)1-188 Me Me H 2-CO₂Me Ph(2-CF₃) 1-189 Me Me H 2-CO₂Me Ph(2-F-6-Cl) 1-190Me Me H 2-CO₂Et Ph(2-F) 1-191 Me Me H 2-CO₂Et Ph(2,6-F₂) 1-192 Me Me H2-CO₂Et Ph(2-C1) 1-193 Me Me H 2-CO₂Et Ph(2-Me) 1-194 Me Me H 2-CO₂EtPh(2-CF₃) 1-195 Me Me H 2-CO₂Et Ph(2-F-6-Cl) 1-196 Me Me H 2-CONH₂Ph(2-F) 1-197 Me Me H 2-CONH₂ Ph(2,6-F₂) 1-198 Me Me H 2-CONH₂ Ph(2-Cl)1-199 Me Me H 2-CONH₂ Ph(2-Me) 1-200 Me Me H 2-CONH₂ Ph(2-CF₃) 1-201 MeMe H 2-CONH₂ Ph(2-F-6-Cl) 1-202 Me Me H 2-CONHMe Ph(2-F) 1-203 Me Me H2-CONHMe Ph(2,6-F₂) 1-204 Me Me H 2-CONHMe Ph(2-Cl) 1-205 Me Me H2-CONHMe Ph(2-Me) 1-206 Me Me H 2-CONHMe Ph(2-CF₃) 1-207 Me Me H2-CONHMe Ph(2-F-6-Cl) 1-208 Me Me H 2-CONMe₂ Ph(2-F) 1-209 Me Me H2-CONMe₂ Ph(2,6-F₂) 1-210 Me Me H 2-CONMe₂ Ph(2-Cl) 1-211 Me Me H2-CONMe₂ Ph(2-Me) 1-212 Me Me H 2-CONMe₂ Ph(2-CF₃) 1-213 Me Me H2-CONMe₂ Ph(2-F-6-Cl) 1-214 Me Me H 3-CO₂H Ph(2-F) 1-215 Me Me H 3-CO₂HPh(2,6-F₂) 1-216 Me Me H 3-CO₂H Ph(2-Cl) 1-217 Me Me H 3-CO₂H Ph(2-Me)1-218 Me Me H 3-CO₂H Ph(2-CF₃₎ 1-219 Me Me H 3-CO₂H Ph(2-F-6-Cl) 1-220Me Me H 3-CO₂Me Ph(2-F) 1-221 Me Me H 3-CO₂Me Ph(2,6-F₂) Oil 1-222 Me MeH 3-CO₂Me Ph(2-Cl) 1-223 Me Me H 3-CO₂Me Ph(2-Me) 1-224 Me Me H 3-CO₂MePh(2-CF₃) 1-225 Me Me H 3-CO₂Me Ph(2-F-6-Cl) 1-226 Me Me H 3-CO₂EtPh(2-F) 1-227 Me Me H 3-CO₂Et Ph(2,6-F₂) 1-228 Me Me H 3-CO₂Et Ph(2-Cl)1-229 Me Me H 3-CO₂Et Ph(2-Me) 1-230 Me Me H 3-CO₂Et Ph(2-CF₃) 1-231 MeMe H 3-CO₂Et Ph(2-F-6-Cl) 1-232 Me Me H 3-CONH₂ Ph(2-F) 1-233 Me Me H3-CONH₂ Ph(2,6-F₂) 1-234 Me Me H 3-CONH₂ Ph(2-Cl) 1-235 Me Me H 3-CONH₂Ph(2-Me) 1-236 Me Me H 3-CONH₂ Ph(2-CF₃) 1-237 Me Me H 3-CONH₂Ph(2-F-6-Cl) 1-238 Me Me H 3-CONHMe Ph(2-F) 1-239 Me Me H 3-CONHMePh(2,6-F₂) 1-240 Me Me H 3-CONHMe Ph(2-Cl) 1-241 Me Me H 3-CONHMePh(2-Me) 1-242 Me Me H 3-CONHMe Ph(2-CF₃) 1-243 Me Me H 3-CONHMePh(2-F-6-Cl) 1-244 Me Me H 3-CONMe₂ Ph(2-F) 1-245 Me Me H 3-CONMe₂Ph(2,6-F₂) 1-246 Me Me H 3-CONMe₂ Ph(2-Cl) 1-247 Me Me H 3-CONMe₂Ph(2-Me) 1-248 Me Me H 3-CONMe₂ Ph(2-CF₃) 1-249 Me Me H 3-CONMe₂Ph(2-F-6-Cl)

TABLE 2

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 2-1 Me Me H 4-ClPh(2-F) 2-2 Me Et H 4-Cl Ph(2-F) 2-3 —(CH₂)₂— H 4-Cl Ph(2-F) 2-4 Me Me H4-Cl Ph(2-6-F₂) 144-153 2-5 Me Me H 4-Cl Ph(2-Cl) 2-6 Me Et H 4-ClPh(2-C1) 2-7 Me Me COMe 4-Cl Ph(2-Cl) 2-8 —(CH₂)₂— H 4-Cl Ph(2-Cl) 2-9—(CH₂)₄— H 4-Cl Ph(2-Cl) 2-10 Me Me H 4-Cl Ph(2-CF₃) 2-11 Me Me H 4-BrPh(2-F) 2-12 Me Me H 4-Br Ph(2,6-F₂) 2-13 Me Me H 4-Br Ph(2-Cl) 2-14 MeMe H 4-Br Ph(2-CF₃) 2-15 Me Me H 4-F Ph(2-F) 2-16 Me Me H 4-F Ph(2,6-F₂)2-17 Me Me H 4-F Ph(2-Cl) 2-18 Me Me H 4-F Ph(2-CF₃) 2-19 Me Me H 4-CF₃Ph(2-F) 2-20 Me Me H 4-CF₃ Ph(2,6-F₂) 2-21 Me Me H 4-CF₃ Ph(2-Cl) 2-22Me Me H 4-CF₃ Ph(2-CF₃) 2-23 Me Me H 3,4-Cl₂ Ph(2-F) 2-24 Me Me H3,4-Cl₂ Ph(2,6-F₂) 2-25 —(CH₂)₂— H 3,4-Cl₂ Ph(2-Cl) 2-26 —(CH₂)₅— H3,4-Cl₂ Ph(2-CF₃) 2-27 Me Me Me 2,4-Cl₂ Ph(2-F) 2-28 Me Me H 2,4-Cl₂Ph(2-F) 2-29 Me Me H 2,4-Cl₂ Ph(2,6-F₂) 2-30 Me Me H 2,4-Cl₂ Ph(2-Cl)2-31 Me Me H 2,4-Cl₂ Ph(2-CF₃) 2-32 Me Me H 2,4-F₂ Ph(2-F) 2-33 Me Me H2,4-F₂ Ph(2,6-F₂) 2-34 Me Me H 4-OCF₃ Ph(2-F) 2-35 Me Me H 4-OCF₃Ph(2,6-F₂) 2-36 Me Me H 4-OCF₃ Ph(2-Cl) 2-37 Me Me H 4-OCF₃ Ph(2-Me)2-38 Me Me H 4-OCF₃ Ph(2-CF₃) 2-39 Me Me H 4-OCF₃ Ph(2-F-6-Cl) 2-40 MeMe H 4-OCHF₂ Ph(2-F) 2-41 Me Me H 4-OCHF₂ Ph(2,6-F₂) 2-42 Me Me H4-OCHF₂ Ph(2-Cl) 2-43 Me Me H 4-OCHF₂ Ph(2-Me) 2-44 Me Me H 4-OCHF₂Ph(2-CF₃) 2-45 Me Me H 4-OCHF₂ Ph(2-F-6-Cl) 2-46 Me Me H 4-OCH₂CF₃Ph(2-F) 2-47 Me Me H 4-OCH₂CF₃ Ph(2,6-F₂) 2-48 Me Me H 4-OCH₂CF₃Ph(2-Cl) 2-49 Me Me H 4-OCH₂CF₃ Ph(2-Me) 2-50 Me Me H 4-OCH₂CF₃Ph(2-CF₃) 2-51 Me Me H 4-OCH₂CF₃ Ph(2-F-6-Cl) 2-52 Me Me H 2-Me-4-ClPh(2-F) 2-53 Me Me H 2-Me-4-Cl Ph(2,6-F₂) 2-54 Me Me H 2-Me-4-ClPh(2-Cl) 2-55 Me Me H 2-Me-4-Cl Ph(2-Me) 2-56 Me Me H 2-Me-4-ClPh(2-CF₃) 2-57 Me Me H 2-Me-4-Cl Ph(2-F-6-Cl) 2-58 Me Me H 2-Me-4-BrPh(2-F) 2-59 Me Me H 2-Me-4-Br Ph(2,6-F₂) 2-60 Me Me H 2-Me-4-BrPh(2-Cl) 2-61 Me Me H 2-Me-4-Br Ph(2-Me) 2-62 Me Me H 2-Me-4-BrPh(2-CF₃) 2-63 Me Me H 2-Me-4-Br Ph(2-F-6-Cl) 2-64 Me Me H 2-Me-4-OCF₃Ph(2-F) 2-65 Me Me H 2-Me-4-OCF₃ Ph(2,6-F₂) 2-66 Me Me H 2-Me-4-OCF₃Ph(2-Cl) 2-67 Me Me H 2-Me-4-OCF₃ Ph(2-Me) 2-68 Me Me H 2-Me-4-OCF₃Ph(2-CF₃) 2-69 Me Me H 2-Me-4-OCF₃ Ph(2-F-6-Cl) 2-70 Me Me H2-Me-4-OCHF₂ Ph(2-F) 2-71 Me Me H 2-Me-4-OCHF₂ Ph(2-6-F₂) 2-72 Me Me H2-Me-4-OCHF₂ Ph(2-Cl) 2-73 Me Me H 2-Me-4-OCHF₂ Ph(2-Me) 2-74 Me Me H2-Me-4-OCHF₂ Ph(2-CF₃) 2-75 Me Me H 2-Me-4-OCHF₂ Ph(2-F-6-Cl) 2-76 Me MeH 2-Me-4-OCH₂CF₃ Ph(2-F) 2-77 Me Me H 2-Me-4-OCH₂CF₃ Ph(2,6-F₂) 2-78 MeMe H 2-Me-4-OCH₂CF₃ Ph(2-Cl) 2-79 Me Me H 2-Me-4-OCH₂CF₃ Ph(2-Me) 2-80Me Me H 2-Me-4-OCH₂CF₃ Ph(2-CF₃) 2-81 Me Me H 2-Me-4-OCH₂CF₃Ph(2-F-6-Cl) 2-82 Me Me H 2-Me-4-CF₃ Ph(2-F) 2-83 Me Me H 2-Me-4-CF₃Ph(2,6-F₂) 2-84 Me Me H 2-Me-4-CF₃ Ph (2-Cl) 2-85 Me Me H 2-Me-4-CF₃Ph(2-Me) 2-86 Me Me H 2-Me-4-CF₃ Ph(2-CF₃) 2-87 Me Me H 2-Me-4-CF₃Ph(2-F-6-Cl) 2-88 Me Me H 2-Cl-4-Br Ph(2-F) 2-89 Me Me H 2-Cl-4-BrPh(2,6-F₂) 2-90 Me Me H 2-Cl-4-Br Ph(2-Cl) 2-91 Me Me H 2-Cl-4-BrPh(2-Me) 2-92 Me Me H 2-Cl-4-Br Ph(2-CF₃) 2-93 Me Me H 2-Cl-4-BrPh(2-F-6-Cl) 2-94 Me Me H 2-Cl-4-OCF₃ Ph(2-F) 2-95 Me Me H 2-Cl-4-OCF₃Ph(2,6-F₂) 2-96 Me Me H 2-Cl-4-OCF₃ Ph(2-Cl) 2-97 Me Me H 2-Cl-4-OCF₃Ph(2-Me) 2-98 Me Me H 2-Cl-4-OCF₃ Ph(2-CF₃) 2-99 Me Me H 2-Cl-4-OCF₃Ph(2-F-6-Cl) 2-100 Me Me H 2-Cl-4-OCHF₂ Ph(2-F) 2-101 Me Me H2-Cl-4-OCHF₂ Ph(2,6-F₂) 2-102 Me Me H 2-Cl-4-OCHF₂ Ph(2-Cl) 2-103 Me MeH 2-Cl-4-OCHF₂ Ph(2-Me) 2-104 Me Me H 2-Cl-4-OCHF₂ Ph(2-CF₃) 2-105 Me MeH 2-Cl-4-OCHF₂ Ph(2-F-6-Cl) 2-106 Me Me H 2-Cl-4-OCH₂CF₃ Ph(2-F) 2-107Me Me H 2-Cl-4-OCH₂CF₃ Ph(2,6-F₂) 2-108 Me Me H 2-Cl-4-OCH₂CF₃ Ph(2-Cl)2-109 Me Me H 2-Cl-4-OCH₂CF₃ Ph(2-Me) 2-110 Me Me H 2-Cl-4-OCH₂CF₃Ph(2-CF₃) 2-111 Me Me H 2-Cl-4-OCH₂CF₃ Ph(2-F-6-Cl)

TABLE 3

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 3-1 Me Me H H Ph3-2 Me Me H H Ph(2-F) <30 yellow resin 3-3 Me Me H H Ph(2-Cl) 3-4 Me MeH H Ph(2-OMe) 3-5 Me Me H H Ph(2,6-F₂) 3-6 Me Me H H Ph(2,6-Cl₂) 3-7 MeMe H H Ph(2,6-OMe₂) 3-8 Me Me H 6-Cl Ph 3-9 Me Me H 6-Cl Ph(2-F) 3-10 MeMe H 6-Cl Ph(2-Cl) 3-11 Me Me H 6-Cl Ph(2,6-F₂) 3-12 Me Me H 6-ClPh(2,6-Cl₂) 3-13 Me Me H 6-Br Ph 3-14 Me Me H 6-Br Ph(2-F) 3-15 Me Me H6-Br Ph(2-Cl) 3-16 Me Me H 6-Br Ph(2,6-F₂) 3-17 Me Me H 6-Br Ph(2,6-Cl₂)3-18 Me Me H 6-CF₃ Ph(2,6-F₂) 3-19 Me Me H 6-CN Ph(2,6-F₂) 3-20 Me CN HH Ph(2,6-F₂) 3-21 Me CO₂Et H H Ph(2,6-F₂) 3-22 Me CN H 6-Cl Ph(2,6-F₂)3-23 Me CO₂Et H 6-Cl Ph(2,6-F₂) 3-24 Me Et H H Ph(2,6-F₂) 3-25 Me MeCOMe H Ph(2,6-F₂) 3-26 Me Me CH₂OMe H Ph(2,6-F₂) 3-27 Me Me H H1-naphthyl 3-28 Me Me H H 2-naphthyl 3-29 Me Me H H 2-thienyl 3-30 Me MeH H 3-thienyl 3-31 Me Me H H 2-pyrazinyl 3-32 Me Me H H 2-pyridyl 3-33Me Me H H 3-pyridyl 3-34 Me Me H H 4- trifluoromethyl- 3-pyridyl 3-35 MeMe H H 4-pyridyl 3-36 Me Me H H 2-furyl 3-37 Me Me H H 3-furyl 3-38 MeMe H 2-Cl Ph(2-F) 3-39 Me Me H 2-Cl Ph(2,6-F₂) 3-40 Me Me H 2-ClPh(2-Cl) 3-41 Me Me H 2-Cl Ph(2-Me) 3-42 Me Me H 2-Cl Ph(2-CF₃) 3-43 MeMe H 2-Cl Ph(2-F-6-Cl) 3-44 Me Me H 2-Br Ph(2-F) 3-45 Me Me H 2-BrPh(2,6-F₂) 3-46 Me Me H 2-Br Ph(2-Cl) 3-47 Me Me H 2-Br Ph(2-Me) 3-48 MeMe H 2-Br Ph(2-CF₃) 3-49 Me Me H 2-Br Ph(2-F-6-Cl) 3-50 Me Me H 2-CF₃Ph(2-F) 3-51 Me Me H 2-CF₃ Ph(2,6-F₂) 3-52 Me Me H 2-CF₃ Ph(2-Cl) 3-53Me Me H 2-CF₃ Ph(2-Me) 3-54 Me Me H 2-CF₃ Ph(2-CF₃) 3-55 Me Me H 2-CF₃Ph(2-F-6-Cl) 3-56 Me Me H 2-OCF₃ Ph(2-F) 3-57 Me Me H 2-OCF₃ Ph(2,6-F₂)3-58 Me Me H 2-OCF₃ Ph(2-Cl) 3-59 Me Me H 2-OCF₃ Ph(2-Me) 3-60 Me Me H2-OCF₃ Ph(2-CF₃) 3-61 Me Me H 2-OCF₃ Ph(2-F-6-Cl) 3-62 Me Me H 2-OCHF₂Ph(2-F) 3-63 Me Me H 2-OCHF₂ Ph(2,6-F₂) 3-64 Me Me H 2-OCHF₂ Ph(2-Cl)3-65 Me Me H 2-OCHF₂ Ph(2-Me) 3-66 Me Me H 2-OCHF₂ Ph(2-CF₃) 3-67 Me MeH 2-OCHF₂ Ph(2-F-6-Cl) 3-68 Me Me H 2-OCH₂CF₃ Ph(2-F) 3-69 Me Me H2-OCH₂CF₃ Ph(2,6-F₂) 3-70 Me Me H 2-OCH₂CF₃ Ph(2-Cl) 3-71 Me Me H2-OCH₂CF₃ Ph(2-Me) 3-72 Me Me H 2-OCH₂CF₃ Ph(2-CF₃) 3-73 Me Me H2-OCH₂CF₃ Ph(2-F-6-Cl) 3-74 Me Me H 2-CN Ph(2-F) 3-75 Me Me H 2-CNPh(2,6-F₂) 3-76 Me Me H 2-CN Ph(2-Cl) 3-77 Me Me H 2-CN Ph(2-Me) 3-78 MeMe H 2-CN Ph(2-CF₃) 3-79 Me Me H 2-CN Ph(2-F-6-Cl) 3-80 Me Me H 3-ClPh(2-F) 3-81 Me Me H 3-Cl Ph(2,6-F₂) 3-82 Me Me H 3-Cl Ph(2-Cl) 3-83 MeMe H 3-Cl Ph(2-Me) 3-84 Me Me H 3-Cl Ph(2-CF₃) 3-85 Me Me H 3-ClPh(2-F-6-Cl) 3-86 Me Me H 3-Br Ph(2-F) 3-87 Me Me H 3-Br Ph(2,6-F₂) 3-88Me Me H 3-Br Ph(2-Cl) 3-89 Me Me H 3-Br Ph(2-Me) 3-90 Me Me H 3-BrPh(2-CF₃) 3-91 Me Me H 3-Br Ph(2-F-6-Cl) 3-92 Me Me H 3-CF₃ Ph(2-F) 3-93Me Me H 3-CF₃ Ph(2,6-F₂) 3-94 Me Me H 3-CF₃ P1-1(2-Cl) 3-95 Me Me H3-CF₃ Ph(2-Me) 3-96 Me Me H 3-CF₃ Ph(2-CF₃) 3-97 Me Me H 3-CF₃Ph(2-F-6-Cl) 3-98 Me Me H 2-OCF₃ Ph(2-F) 3-99 Me Me H 2-OCF₃ Ph(2,6-F₂)3-100 Me Me H 2-OCF₃ Ph(2-Cl) 3-101 Me Me H 2-OCF₃ Ph(2-Me) 3-102 Me MeH 2-OCF₃ Ph(2-CF₃) 3-103 Me Me H 2-OCF₃ Ph(2-F-6-Cl) 3-104 Me Me H3-OCHF₂ Ph(2-F) 3-105 Me Me H 3-OCHF₂ Ph(2,6-F₂) 3-106 Me Me H 3-OCHF₂Ph(2-Cl) 3-107 Me Me H 3-OCHF₂ Ph(2-Me) 3-108 Me Me H 3-OCHF₂ Ph(2-CF₃)3-109 Me Me H 3-OCHF₂ Ph(2-F-6-Cl) 3-110 Me Me H 3-OCH₂CF₃ Ph(2-F) 3-111Me Me H 3-OCH₂CF₃ Ph(2,6-F₂) 3-112 Me Me H 3-OCH₂CF₃ Ph(2-Cl) 3-113 MeMe H 3-OCH₂CF₃ Ph(2-Me) 3-114 Me Me H 3-OCH₂CF₃ Ph(2-CF₃) 3-115 Me Me H3-OCH₂CF₃ Ph(2-F-6-Cl) 3-116 Me Me H 3-CN Ph(2-F) 3-117 Me Me H 3-CNPh(2,6-F₂) 3-118 Me Me H 3-CN Ph(2-Cl) 3-119 Me Me H 3-CN Ph(2-Me) 3-120Me Me H 3-CN Ph(2-CF₃) 3-121 Me Me H 3-CN Ph(2-F-6-Cl) 3-122 Me Me H4-Cl Ph(2-F) 3-123 Me Me H 4-Cl Ph(2,6-F₂) 3-124 Me Me H 4-Cl Ph(2-Cl)3-125 Me Me H 4-Cl Ph(2-Me) 3-126 Me Me H 4-Cl Ph(2-CF₃) 3-127 Me Me H4-Cl Ph(2-F-6-Cl) 3-128 Me Me H 4-Br Ph(2-F) 3-129 Me Me H 4-BrPh(2,6-F₂) 3-130 Me Me H 4-Br Ph(2-Cl) 3-131 Me Me H 4-Br Ph(2-Me) 3-132Me Me H 4-Br Ph(2-CF₃) 3-133 Me Me H 4-Br Ph(2-F-6-Cl) 3-134 Me Me H4-CF₃ Ph(2-F) 3-135 Me Me H 4-CF₃ Ph(2,6-F₂) 3-136 Me Me H 4-CF₃Ph(2-Cl) 3-137 Me Me H 4-CF₃ Ph(2-Me) 3-138 Me Me H 4-CF₃ Ph(2-CF₃)3-139 Me Me H 4-CF₃ Ph(2-F-6-Cl) 3-140 Me Me H 4-OCF₃ Ph(2-F) 3-141 MeMe H 4-OCF₃ Ph(2,6-F₂) 3-142 Me Me H 4-OCF₃ Ph(2-Cl) 3-143 Me Me H4-OCF₃ Ph(2-Me) 3-144 Me Me H 4-OCF₃ Ph(2-CF₃) 3-145 Me Me H 4-OCF₃Ph(2-F-6-Cl) 3-146 Me Me H 4-OCHF₂ Ph(2-F) 3-147 Me Me H 4-OCHF₂Ph(2,6-F₂) 3-148 Me Me H 4-OCHF₂ Ph(2-Cl) 3-149 Me Me H 4-OCHF₂ Ph(2-Me)3-150 Me Me H 4-OCHF₂ Ph(2-CF₃) 3-151 Me Me H 4-OCHF₂ Ph(2-F-6-Cl) 3-152Me Me H 4-OCH₂CF₃ Ph(2-F) 3-153 Me Me H 4-OCH₂CF₃ Ph(2,6-F₂) 3-154 Me MeH 4-OCH₂CF₃ Ph(2-Cl) 3-155 Me Me H 4-OCH₂CF₃ Ph(2-Me) 3-156 Me Me H4-OCH₂CF₃ Ph(2-CF₃) 3-157 Me Me H 4-OCH₂CF₃ Ph(2-F-6-Cl) 3-158 Me Me H4-CN Ph(2-F) 3-159 Me Me H 4-CN Ph(2,6-F₂) 3-160 Me Me H 4-CN Ph(2-Cl)3-161 Me Me H 4-CN Ph(2-Me) 3-162 Me Me H 4-CN Ph(2-CF₃) 3-163 Me Me H4-CN Ph(2-F-6-Cl) 3-164 Me Me H 5-Cl Ph(2-F) 3-165 Me Me H 5-ClPh(2,6-F₂) 3-166 Me Me H 5-Cl Ph(2-Cl) 3-167 Me Me H 5-Cl Ph(2-Me) 3-168Me Me H 5-Cl Ph(2-CF₃) 3-169 Me Me H 5-Cl Ph(2-F-6-Cl) 3-170 Me Me H5-Br Ph(2-F) 3-171 Me Me H 5-Br Ph(2,6-F₂) 3-172 Me Me H 5-Br Ph(2-Cl)3-173 Me Me H 5-Br Ph(2-Me) 3-174 Me Me H 5-Br Ph(2-CF₃) 3-175 Me Me H5-Br Ph(2-F-6-Cl) 3-176 Me Me H 5-CF₃ Ph(2-F) 3-177 Me Me H 5-CF₃Ph(2,6-F₂) 3-178 Me Me H 5-CF₃ Ph(2-Cl) 3-179 Me Me H 5-CF₃ Ph(2-Me)3-180 Me Me H 5-CF₃ Ph(2-CF₃) 3-181 Me Me H 5-CF₃ Ph(2-F-6-Cl) 3-182 MeMe H 5-OCF₃ Ph(2-F) 3-183 Me Me H 5-OCF₃ Ph(2,6-F₂) 3-184 Me Me H 5-OCF₃Ph(2-Cl) 3-185 Me Me H 5-OCF₃ Ph(2-Me) 3-186 Me Me H 5-OCF₃ Ph(2-CF₃)3-187 Me Me H 5-OCF₃ Ph(2-F-6-Cl) 3-188 Me Me H 5-OCHF₂ Ph(2-F) 3-189 MeMe H 5-OCHF₂ Ph(2,6-F₂) 3-190 Me Me H 5-OCHF₂ Ph(2-Cl) 3-191 Me Me H5-OCHF₂ Ph(2-Me) 3-192 Me Me H 5-OCHF₂ Ph(2-CF₃) 3-193 Me Me H 5-OCHF₂Ph(2-F-6-Cl) 3-194 Me Me H 5-OCH₂CF₃ Ph(2-F) 3-195 Me Me H 5-OCH₂CF₃Ph(2,6-F₂) 3-196 Me Me H 5-OCH₂CF₃ Ph(2-Cl) 3-197 Me Me H 5-OCH₂CF₃Ph(2-Me) 3-198 Me Me H 5-OCH₂CF₃ Ph(2-CF₃) 3-199 Me Me H 5-OCH₂CF₃Ph(2-F-6-Cl) 3-200 Me Me H 5-CN Ph(2-F) 3-201 Me Me H 5-CN Ph(2,6-F₂)3-202 Me Me H 5-CN Ph(2-Cl) 3-203 Me Me H 5-CN Ph(2-Me) 3-204 Me Me H5-CN Ph(2-CF₃) 3-205 Me Me H 5-CN Ph(2-F-6-Cl) 3-206 Me Me H 6-ClPh(2-F) 3-207 Me Me H 6-Cl Ph(2,6-F₂) 3-208 Me Me H 6-Cl Ph(2-Cl) 3-209Me Me H 6-Cl Ph(2-Me) 3-210 Me Me H 6-Cl Ph(2-CF₃) 3-211 Me Me H 6-ClPh(2-F-6-Cl) 3-212 Me Me H 6-Br Ph(2-F) 3-213 Me Me H 6-Br Ph(2,6-F₂)3-214 Me Me H 6-Br Ph(2-Cl) 3-215 Me Me H 6-Br Ph(2-Me) 3-216 Me Me H6-Br Ph(2-CF₃) 3-217 Me Me H 6-Br Ph(2-F-6-Cl) 3-218 Me Me H 6-CF₃Ph(2-F) 3-219 Me Me H 6-CF₃ Ph(2,6-F₂) 3-220 Me Me H 6-CF₃ Ph(2-Cl)3-221 Me Me H 6-CF₃ Ph(2-Me) 3-222 Me Me H 6-CF₃ Ph(2-CF₃) 3-223 Me Me H6-CF₃ Ph(2-F-6-Cl) 3-224 Me Me H 6-OCF₃ Ph(2-F) 3-225 Me Me H 6-OCF₃Ph(2,6-F₂) 3-226 Me Me H 6-OCF₃ Ph(2-Cl) 3-227 Me Me H 6-OCF₃ Ph(2-Me)3-228 Me Me H 6-OCF₃ Ph(2-CF₃) 3-229 Me Me H 6-OCF₃ Ph(2-F-6-Cl) 3-230Me Me H 6-OCHF₂ Ph(2-F) 3-231 Me Me H 6-OCHF₂ Ph(2,6-F₂) 3-232 Me Me H6-OCHF₂ Ph(2-Cl) 3-233 Me Me H 6-OCHF₂ Ph(2-Me) 3-234 Me Me H 6-OCHF₂Ph(2-CF₃) 3-235 Me Me H 6-OCHF₂ Ph(2-F-6-Cl) 3-236 Me Me H 6-OCH₂CF₃Ph(2-F) 3-237 Me Me H 6-OCH₂CF₃ Ph(2,6-F₂) 3-238 Me Me H 6-OCH₂CF₃Ph(2-Cl) 3-239 Me Me H 6-OCH₂CF₃ Ph(2-Me) 3-240 Me Me H 6-OCH₂CF₃Ph(2-CF₃) 3-241 Me Me H 6-OCH₂CF₃ Ph(2-F-6-Cl) 3-242 Me Me H 6-CNPh(2-F) 3-243 Me Me H 6-CN Ph(2,6-F₂) 3-244 Me Me H 6-CN Ph(2-Cl) 3-245Me Me H 6-CN Ph(2-Me) 3-246 Me Me H 6-CN Ph(2-CF₃) 3-247 Me Me H 6-CNPh(2-F-6-Cl) 3-248 Me Me H 7-Cl Ph(2-F) 3-249 Me Me H 7-Cl Ph(2,6-F₂)3-250 Me Me H 7-Cl Ph(2-Cl) 3-251 Me Me H 7-Cl Ph(2-Me) 3-252 Me Me H7-Cl Ph(2-CF₃) 3-253 Me Me H 7-Cl Ph(2-F-6-Cl) 3-254 Me Me H 7-BrPh(2-F) 3-255 Me Me H 7-Br Ph(2,6-F₂) 3-256 Me Me H 7-Br Ph(2-Cl) 3-257Me Me H 7-Br Ph(2-Me) 3-258 Me Me H 7-Br Ph(2-CF₃) 3-259 Me Me H 7-BrPh(2-F-6-Cl) 3-260 Me Me H 7-CF₃ Ph(2-F) 3-261 Me Me H 7-CF₃ Ph(2,6-F₂)3-262 Me Me H 7-CF₃ Ph(2-Cl) 3-263 Me Me H 7-CF₃ Ph(2-Me) 3-264 Me Me H7-CF₃ Ph(2-CF₃) 3-265 Me Me H 7-CF₃ Ph(2-F-6-Cl) 3-266 Me Me H 7-OCF₃Ph(2-F) 3-267 Me Me H 7-OCF₃ Ph(2,6-F₂) 3-268 Me Me H 7-OCF₃ Ph(2-Cl)3-269 Me Me H 7-OCF₃ Ph(2-Me) 3-270 Me Me H 7-OCF₃ Ph(2-CF₃) 3-271 Me MeH 7-OCF₃ Ph(2-F-6-Cl) 3-272 Me Me H 7-OCHF₂ Ph(2-F) 3-273 Me Me H7-OCHF₂ Ph(2,6-F₂) 3-274 Me Me H 7-OCHF₂ Ph(2-Cl) 3-275 Me Me H 7-OCHF₂Ph(2-Me) 3-276 Me Me H 7-OCHF₂ Ph(2-CF₃) 3-277 Me Me H 7-OCHF₂Ph(2-F-6-Cl) 3-278 Me Me H 7-OCH₂CF₃ Ph(2-F) 3-279 Me Me H 7-OCH₂CF₃Ph(2,6-F₂) 3-280 Me Me H 7-OCH₂CF₃ Ph(2-Cl) 3-281 Me Me H 7-OCH₂CF₃Ph(2-Me) 3-282 Me Me H 7-OCH₂CF₃ Ph(2-CF₃) 3-283 Me Me H 7-OCH₂CF₃Ph(2-F-6-Cl) 3-284 Me Me H 7-CN Ph(2-F) 3-235 Me Me H 7-CN Ph(2,6-F₂)3-286 Me Me H 7-CN Ph(2-Cl) 3-287 Me Me H 7-CN Ph(2-Me) 3-288 Me Me H7-CN Ph(2-CF₃) 3-289 Me Me H 7-CN Ph(2-F-6-Cl) 3-290 Me Me H 2-Me-4-ClPh(2-F) 3-291 Me Me H 2-Me-4-Cl Ph(2,6-F₂) 3-292 Me Me H 2-Me-4-ClPh(2-Cl) 3-293 Me Me H 2-Me-4-Cl P142-Me) 3-294 Me Me H 2-Me-4-ClPh(2-CF₃) 3-295 Me Me H 2-Me-4-Cl Ph(2-F-6-Cl) 3-296 Me Me H 3-Me-4-ClPh(2-F) 3-297 Me Me H 3-Me-4-Cl Ph(2,6-F₂) 3-298 Me Me H 3-Me-4-ClP142-Cl) 3-299 Me Me H 3-Me-4-Cl Ph(2-Me) 3-300 Me Me H 3-Me-4-ClPh(2-CF₃) 3-301 Me Me H 3-Me-4-Cl Ph(2-F-6-Cl) 3-302 Me Me H 5-Me-6-ClPh(2-F) 3-303 Me Me H 5-Me-6-Cl Ph(2,6-F₂) 3-304 Me Me H 5-Me-6-ClPh(2-Cl) 3-305 Me Me H 5-Me-6-Cl Ph(2-Me) 3-306 Me Me H 5-Me-6-ClPh(2-CF₃) 3-307 Me Me H 5-Me-6-Cl Ph(2-F-6-Cl) 3-308 Me Me H 6-Me-5-ClPh(2-F) 3-309 Me Me H 6-Me-5-Cl Ph(2,6-F₂) 3-310 Me Me H 6-Me-5-ClPh(2-C1) 3-311 Me Me H 6-Me-5-Cl Ph(2-Me) 3-312 Me Me H 6-Me-5-ClPh(2-CF₃) 3-313 Me Me H 6-Me-5-Cl Ph(2-F-6-Cl) 3-314 Me Me H 2-Me-4-BrPh(2-F) 3-315 Me Me H 2-Me-4-Br Ph(2,6-F₂) 3-316 Me Me H 2-Me-4-BrPh(2-Cl) 3-317 Me Me H 2-Me-4-Br Ph(2-Me) 3-318 Me Me H 2-Me-4-BrPh(2-CF₃) 3-319 Me Me H 2-Me-4-Br Ph(2-F-6-Cl) 3-320 Me Me H 3-Me-4-BrPh(2-F) 3-321 Me Me H 3-Me-4-Br Ph(2,6-F₂) 3-322 Me Me H 3-Me-4-BrPh(2-Cl) 3-323 Me Me H 3-Me-4-Br Ph(2-Me) 3-324 Me Me H 3-Me-4-BrPh(2-CF₃) 3-325 Me Me H 3-Me-4-Br Ph(2-F-6-Cl) 3-326 Me Me H 5-Me-6-BrPh(2-F) 3-327 Me Me H 5-Me-6-Br Ph(2,6-F₂) 3-328 Me Me H 5-Me-6-BrPh(2-Cl) 3-329 Me Me H 5-Me-6-Br Ph(2-Me) 3-330 Me Me H 5-Me-6-BrPh(2-CF₃) 3-331 Me Me H 5-Me-6-Br Ph(2-F-6-Cl) 3-332 Me Me H 6-Me-5-BrPh(2-F) 3-333 Me Me H 6-Me-5-Br Ph(2,6-F₂) 3-334 Me Me H 6-Me-5-BrPh(2-Cl) 3-335 Me Me H 6-Me-5-Br Ph(2-Me) 3-336 Me Me H 6-Me-5-BrPh(2-CF₃) 3-337 Me Me H 6-Me-5-Br Ph(2-F-6-Cl) 3-338 Me Me H 2-Me-4-CF₃Ph(2-F) 3-339 Me Me H 2-Me-4-CF₃ Ph(2,6-F₂) 3-340 Me Me H 2-Me-4-CF₃Ph(2-Cl) 3-341 Me Me H 2-Me-4-CF₃ Ph(2-Me) 3-342 Me Me H 2-Me-4-CF₃Ph(2-CF₃) 3-343 Me Me H 2-Me-4-CF₃ Ph(2-F-6-Cl) 3-344 Me Me H 3-Me-4-CF₃Ph(2-F) 3-345 Me Me H 3-Me-4-CF₃ Ph(2,6-F₂) 3-346 Me Me H 3-Me-4-CF₃Ph(2-Cl) 3-347 Me Me H 3-Me-4-CF₃ Ph(2-Me) 3-348 Me Me H 3-Me-4-CF₃Ph(2-CF₃) 3-349 Me Me H 3-Me-4-CF₃ Ph(2-F-6-Cl) 3-350 Me Me H 5-Me-6-CF₃Ph(2-F) 3-351 Me Me H 5-Me-6-CF₃ Ph(2,6-F₂) 3-352 Me Me H 5-Me-6-CF₃Ph(2-Cl) 3-353 Me Me H 5-Me-6-CF₃ Ph(2-Me) 3-354 Me Me H 5-Me-6-CF₃Ph(2-CF₃) 3-355 Me Me H 5-Me-6-CF₃ Ph(2-F-6-Cl) 3-356 Me Me H 6-Me-5-CF₃Ph(2-F) 3-357 Me Me H 6-Me-5-CF₃ Ph(2,6-F₂) 3-358 Me Me H 6-Me-5-CF₃Ph(2-Cl) 3-359 Me Me H 6-Me-5-CF₃ Ph(2-Me) 3-360 Me Me H 6-Me-5-CF₃Ph(2-CF₃) 3-361 Me Me H 6-Me-5-CF₃ Ph(2-F-6-Cl) 3-362 Me Me H2-Me-4-OCF₃ Ph(2-F) 3-363 Me Me H 2-Me-4-OCF₃ Ph(2,6-F₂) 3-364 Me Me H2-Me-4-OCF₃ Ph(2-Cl) 3-365 Me Me H 2-Me-4-OCF₃ Ph(2-Me) 3-366 Me Me H2-Me-4-OCF₃ Ph(2-CF₃) 3-367 Me Me H 2-Me-4-OCF₃ Ph(2-F-6-Cl) 3-368 Me MeH 3-Me-4-OCF₃ Ph(2-F) 3-369 Me Me H 3-Me-4-OCF₃ Ph(2,6-F₂) 3-370 Me Me H3-Me-4-OCF₃ Ph(2-Cl) 3-371 Me Me H 3-Me-4-OCF₃ Ph(2-Me) 3-372 Me Me H3-Me-4-OCF₃ Ph(2-CF₃) 3-373 Me Me H 3-Me-4-OCF₃ Ph(2-F-6-Cl) 3-374 Me MeH 5-Me-6-OCF₃ Ph(2-F) 3-375 Me Me H 5-Me-6-OCF₃ Ph(2,6-F₂) 3-376 Me Me H5-Me-6-OCF₃ Ph(2-Cl) 3-377 Me Me H 5-Me-6-OCF₃ Ph(2-Me) 3-378 Me Me H5-Me-6-OCF₃ Ph(2-CF₃) 3-379 Me Me H 5-Me-6-OCF₃ Ph(2-F-6-Cl) 3-380 Me MeH 6-Me-5-OCF₃ Ph(2-F) 3-381 Me Me H 6-Me-5-OCF₃ Ph(2,6-F₂) 3-382 Me Me H6-Me-5-OCF₃ Ph(2-Cl) 3-383 Me Me H 6-Me-5-OCF₃ Ph(2-Me) 3-384 Me Me H6-Me-5-OCF₃ Ph(2-CF₃) 3-385 Me Me H 6-Me-5-OCF₃ Ph(2-F-6-Cl) 3-386 Me MeH 2-Me-4-OCHF₂ Ph(2-F) 3-387 Me Me H 2-Me-4-OCHF₂ Ph(2,6-F₂) 3-388 Me MeH 2-Me-4-OCHF₂ Ph(2-Cl) 3-389 Me Me H 2-Me-4-OCHF₂ Ph(2-Me) 3-390 Me MeH 2-Me-4-OCHF₂ Ph(2-CF₃) 3-391 Me Me H 2-Me-4-OCHF₂ Ph(2-F-6-Cl) 3-392Me Me H 3-Me-4-OCHF₂ Ph(2-F) 3-393 Me Me H 3-Me-4-OCHF₂ Ph(2,6-F₂) 3-394Me Me H 3-Me-4-OCHF₂ Ph(2-Cl) 3-395 Me Me H 3-Me-4-OCHF₂ Ph(2-Me) 3-396Me Me H 3-Me-4-OCHF₂ Ph(2-CF₃) 3-397 Me Me H 3-Me-4-OCHF₂ Ph(2-F-6-Cl)3-398 Me Me H 5-Me-6-OCHF₂ Ph(2-F) 3-399 Me Me H 5-Me-6-OCHF₂ Ph(2,6-F₂)3-400 Me Me H 5-Me-6-OCHF₂ Ph(2-Cl) 3-401 Me Me H 5-Me-6-OCHF₂ Ph(2-Me)3-402 Me Me H 5-Me-6-OCHF₂ Ph(2-CF₃) 3-403 Me Me H 5-Me-6-OCHF₂Ph(2-F-6-Cl) 3-404 Me Me H 6-Me-5-OCHF₂ Ph(2-F) 3-405 Me Me H6-Me-5-OCHF₂ Ph(2,6-F₂) 3-406 Me Me H 6-Me-5-OCHF₂ Ph(2-Cl) 3-407 Me MeH 6-Me-5-OCHF₂ Ph(2-Me) 3-408 Me Me H 6-Me-5-OCHF₂ Ph(2-CF₃) 3-409 Me MeH 6-Me-5-OCHF₂ Ph(2-F-6-Cl) 3-410 Me Me H 2-Me-4-OCH₂CF₃ Ph(2-F) 3-411Me Me H 2-Me-4-OCH₂CF₃ Ph(2,6-F₂) 3-412 Me Me H 2-Me-4-OCH₂CF₃ Ph(2-Cl)3-413 Me Me H 2-Me-4-OCH₂CF₃ Ph(2-Me) 3-414 Me Me H 2-Me-4-OCH₂CF₃Ph(2-CF₃) 3-415 Me Me H 2-Me-4-OCH₂CF₃ Ph(2-F-6-Cl) 3-416 Me Me H3-Me-4-OCH₂CF₃ Ph(2-F) 3-417 Me Me H 3-Me-4-OCH₂CF₃ Ph(2,6-F₂) 3-418 MeMe H 3-Me-4-OCH₂CF₃ Ph(2-Cl) 3-419 Me Me H 3-Me-4-OCH₂CF₃ Ph(2-Me) 3-420Me Me H 3-Me-4-OCH₂CF₃ Ph(2-CF₃) 3-421 Me Me H 3-Me-4-OCH₂CF₃Ph(2-F-6-Cl) 3-422 Me Me H 5-Me-6-OCH₂CF₃ Ph(2-F) 3-423 Me Me H5-Me-6-OCH₂CF₃ Ph(2,6-F₂) 3-424 Me Me H 5-Me-6-OCH₂CF₃ Ph(2-Cl) 3-425 MeMe H 5-Me-6-OCH₂CF₃ Ph(2-Me) 3-426 Me Me H 5-Me-6-OCH₂CF₃ Ph(2-CF₃)3-427 Me Me H 5-Me-6-OCH₂CF₃ Ph(2-F-6-Cl) 3-428 Me Me H 6-Me-5-OCH₂CF₃Ph(2-F) 3-429 Me Me H 6-Me-5-OCH₂CF₃ Ph(2,6-F₂) 3-430 Me Me H6-Me-5-OCH₂CF₃ Ph(2-Cl) 3-431 Me Me H 6-Me-5-OCH₂CF₃ Ph(2-Me) 3-432 MeMe H 6-Me-5-OCH₂CF₃ Ph(2-CF₃) 3-433 Me Me H 6-Me-5-OCH₂CF₃ Ph(2-F-6-Cl)3-434 Me Me H 2,4-Cl₂ Ph(2-F) 3-435 Me Me H 2,4-Cl₂ Ph(2,6-F₂) 3-436 MeMe H 2,4-Cl₂ Ph(2-Cl) 3-437 Me Me H 2,4-Cl₂ Ph(2-Me) 3-438 Me Me H2,4-Cl₂ Ph(2-CF₃) 3-439 Me Me H 2,4-Cl₂ Ph(2-F-6-Cl) 3-440 Me Me H3,4-Cl₂ Ph(2-F) 3-441 Me Me H 3,4-Cl₂ Ph(2,6-F₂) 3-442 Me Me H 3,4-Cl₂Ph(2-Cl) 3-443 Me Me H 3,4-Cl₂ Ph(2-Me) 3-444 Me Me H 3,4-Cl₂ Ph(2-CF₃)3-445 Me Me H 3,4-Cl₂ Ph(2-F-6-Cl) 3-446 Me Me H 5,6-Cl₂ Ph(2-F) 3-447Me Me H 5,6-Cl₂ Ph(2,6-F₂) 3-448 Me Me H 5,6-Cl₂ Ph(2-Cl) 3-449 Me Me H5,6-Cl₂ Ph(2-Me) 3-450 Me Me H 5,6-Cl₂ Ph(2-CF₃) 3-451 Me Me H 5,6-Cl₂Ph(2-F-6-Cl) 3-452 Me Me H 2-Cl-4-Br Ph(2-F) 3-453 Me Me H 2-Cl-4-BrPh(2,6-F₂) 3-454 Me Me H 2-Cl-4-Br Ph(2-Cl) 3-455 Me Me H 2-Cl-4-BrPh(2-Me) 3-456 Me Me H 2-Cl-4-Br Ph(2-CF₃) 3-457 Me Me H 2-Cl-4-BrPh(2-F-6-Cl) 3-458 Me Me H 3-Cl-4-Br Ph(2-F) 3-459 Me Me H 3-Cl-4-BrPh(2,6-F₂) 3-460 Me Me H 3-Cl-4-Br Ph(2-Cl) 3-461 Me Me H 3-Cl-4-BrPh(2-Me) 3-462 Me Me H 3-Cl-4-Br Ph(2-CF₃) 3-463 Me Me H 3-Cl-4-BrPh(2-F-6-Cl) 3-464 Me Me H 5-Cl-6-Br Ph(2-F) 3-465 Me Me H 5-Cl-6-BrPh(2,6-F₂) 3-466 Me Me H S-Cl-6-Br Ph(2-Cl) 3-467 Me Me H 5-Cl-6-BrPh(2-Me) 3-468 Me Me H 5-Cl-6-Br Ph(2-CF₃) 3-469 Me Me H 5-Cl-6-BrPh(2-F-6-Cl) 3-470 Me Me H 6-Cl-5-Br Ph(2-F) 3-471 Me Me H 6-Cl-5-BrPh(2,6-F₂) 3-472 Me Me H 6-Cl-5-Br Ph(2-Cl) 3-473 Me Me H 6-Cl-5-BrPh(2-Me) 3-474 Me Me H 6-Cl-5-Br Ph(2-CF₃) 3-475 Me Me H 6-Cl-5-BrPh(2-F-6-Cl) 3-476 Me Me H 2-C1-4-CF₃ Ph(2-F) 3-477 Me Me H 2-Cl-4-CF₃Ph(2,6-F₂) 3-478 Me Me H 2-Cl-4-CF₃ Ph(2-Cl) 3-479 Me Me H 2-Cl-4-CF₃Ph(2-Me) 3-480 Me Me H 2-Cl-4-CF₃ Ph(2-CF₃) 3-481 Me Me H 2-Cl-4-CF₃Ph(2-F-6-Cl) 3-482 Me Me H 3-Cl-4-CF₃ Ph(2-F) 3-483 Me Me H 3-Cl-4-CF₃Ph(2,6-F₂) 3-484 Me Me H 3-Cl-4-CF₃ Ph(2-Cl) 3-485 Me Me H 3-Cl-4-CF₃Ph(2-Me) 3-486 Me Me H 3-Cl-4-CF₃ Ph(2-CF₃) 3-487 Me Me H 3-Cl-4-CF₃Ph(2-F-6-Cl) 3-488 Me Me H 5-Cl-6-CF₃ Ph(2-F) 3-489 Me Me H 5-Cl-6-CF₃Ph(2,6-F₂) 3-490 Me Me H 5-Cl-6-CF₃ Ph(2-Cl) 3-491 Me Me H 5-Cl-6-CF₃Ph(2-Me) 3-492 Me Me H 5-Cl-6-CF₃ Ph(2-CF₃) 3-493 Me Me H 5-Cl-6-CF₃Ph(2-F-6-Cl) 3-494 Me Me H 6-Cl-5-CF₃ Ph(2-F) 3-495 Me Me H 6-Cl-5-CF₃Ph(2,6-F₂) 3-496 Me Me H 6-Cl-5-CF₃ Ph(2-Cl) 3-497 Me Me H 6-Cl-5-CF₃Ph(2-Me) 3-498 Me Me H 6-Cl-5-CF₃ Ph(2-CF₃) 3-499 Me Me H 6-Cl-5-CF₃Ph(2-F-6-Cl) 3-500 Me Me H 2-Cl-4-OCF₃ Ph(2-F) 3-501 Me Me H 2-Cl-4-OCF₃Ph(2,6-F₂) 3-502 Me Me H 2-Cl-4-OCF₃ Ph(2-Cl) 3-503 Me Me H 2-Cl-4-OCF₃Ph(2-Me) 3-504 Me Me H 2-Cl-4-OCF₃ Ph(2-CF₃) 3-505 Me Me H 2-Cl-4-OCF₃Ph(2-F-6-Cl) 3-506 Me Me H 3-Cl-4-OCF₃ Ph(2-F) 3-507 Me Me H 3-Cl-4-OCF₃Ph(2,6-F₂) 3-508 Me Me H 3-Cl-4-OCF₃ Ph(2-Cl) 3-509 Me Me H 3-Cl-4-OCF₃Ph(2-Me) 3-510 Me Me H 3-Cl-4-OCF₃ Ph(2-CF₃) 3-511 Me Me H 3-Cl-4-OCF₃Ph(2-F-6-Cl) 3-512 Me Me H 5-Cl-6-OCF₃ Ph(2-F) 3-513 Me Me H 5-Cl-6-OCF₃Ph(2,6-F₂) 3-514 Me Me H 5-Cl-6-OCF₃ Ph(2-Cl) 3-515 Me Me H 5-Cl-6-OCF₃Ph(2-Me) 3-516 Me Me H 5-Cl-6-OCF₃ Ph(2-CF₃) 3-517 Me Me H 5-Cl-6-OCF₃Ph(2-F-6-Cl) 3-518 Me Me H 6-Cl-5-OCF₃ Ph(2-F) 3-519 Me Me H 6-Cl-5-OCF₃Ph(2,6-F₂) 3-520 Me Me H 6-Cl-5-OCF₃ Ph(2-Cl) 3-521 Me Me H 6-Cl-5-OCF₃Ph(2-Me) 3-522 Me Me H 6-Cl-5-OCF₃ Ph(2-CF₃) 3-523 Me Me H 6-Cl-5-OCF₃Ph(2-F-6-Cl) 3-524 Me Me H 2-Cl-4-OCHF₂ Ph(2-F) 3-525 Me Me H2-Cl-4-OCHF₂ Ph(2,6-F₂) 3-526 Me Me H 2-Cl-4-OCHF₂ Ph(2-Cl) 3-527 Me MeH 2-Cl-4-OCHF₂ Ph(2-Me) 3-528 Me Me H 2-Cl-4-OCHF₂ Ph(2-CF₃) 3-529 Me MeH 2-Cl-4-OCHF₂ Ph(2-F-6-Cl) 3-530 Me Me H 3-Cl-4-OCHF₂ Ph(2-F) 3-531 MeMe H 3-Cl-4-OCHF₂ Ph(2,6-F₂) 3-532 Me Me H 3-Cl-4-OCHF₂ Ph(2-Cl) 3-533Me Me H 3-Cl-4-OCHF₂ Ph(2-Me) 3-534 Me Me H 3-Cl-4-OCHF₂ Ph(2-CF₃) 3-535Me Me H 3-Cl-4-OCHF₂ Ph(2-F-6-Cl) 3-536 Me Me H 5-Cl-6-OCHF₂ Ph(2-F)3-537 Me Me H 5-Cl-6-OCHF₂ Ph(2,6-F₂) 3-538 Me Me H 5-Cl-6-OCHF₂Ph(2-Cl) 3-539 Me Me H 5-Cl-6-OCHF₂ Ph(2-Me) 3-540 Me Me H 5-Cl-6-OCHF₂Ph(2-CF₃) 3-541 Me Me H 5-Cl-6-OCHF₂ Ph(2-F-6-Cl) 3-542 Me Me H6-Cl-5-OCHF₂ Ph(2-F) 3-543 Me Me H 6-Cl-5-OCHF₂ Ph(2,6-F₂) 3-544 Me Me H6-Cl-5-OCHF₂ Ph(2-Cl) 3-545 Me Me H 6-Cl-5-OCHF₂ Ph(2-Me) 3-546 Me Me H6-Cl-5-OCHF₂ Ph(2-CF₃) 3-547 Me Me H 6-Cl-5-OCHF₂ Ph(2-F-6-Cl) 3-548 MeMe H 2-Cl-4-OCH₂CF₃ Ph(2-F) 3-549 Me Me H 2-Cl-4-OCH₂CF₃ Ph(2,6-F₂)3-550 Me Me H 2-Cl-4-OCH₂CF₃ Ph(2-Cl) 3-551 Me Me H 2-Cl-4-OCH₂CF₃Ph(2-Me) 3-552 Me Me H 2-Cl-4-OCH₂CF₃ Ph(2-CF₃) 3-553 Me Me H2-Cl-4-OCH₂CF₃ Ph(2-F-6-Cl) 3-554 Me Me H 3-Cl-4-OCH₂CF₃ Ph(2-F) 3-555Me Me H 3-Cl-4-OCH₂CF₃ Ph(2,6-F₂) 3-556 Me Me H 3-Cl-4-OCH₂CF₃ Ph(2-Cl)3-557 Me Me H 3-Cl-4-OCH₂CF₃ Ph(2-Me) 3-558 Me Me H 3-Cl-4-OCH₂CF₃Ph(2-CF₃) 3-559 Me Me H 3-Cl-4-OCH₂CF₃ Ph(2-F-6-Cl) 3-560 Me Me H5-Cl-6-OCH₂CF₃ Ph(2-F) 3-561 Me Me H 5-Cl-6-OCH₂CF₃ Ph(2,6-F₂) 3-562 MeMe H 5-Cl-6-OCH₂CF₃ Ph(2-Cl) 3-563 Me Me H 5-Cl-6-OCH₂CF₃ Ph(2-Me) 3-564Me Me H 5-Cl-6-OCH₂CF₃ Ph(2-CF₃) 3-565 Me Me H 5-Cl-6-OCH₂CF₃Ph(2-F-6-Cl) 3-566 Me Me H 6-Cl-5-OCH₂CF₃ Ph(2-F) 3-567 Me Me H6-Cl-5-OCH₂CF₃ Ph(2,6-F₂) 3-568 Me Me H 6-Cl-5-OCH₂CF₃ Ph(2-Cl) 3-569 MeMe H 6-Cl-5-OCH₂CF₃ Ph(2-Me) 3-570 Me Me H 6-Cl-5-OCH₂CF₃ Ph(2-CF₃)3-571 Me Me H 6-Cl-5-OCH₂CF₃ Ph(2-F-6-Cl)

TABLE 4

Com- Physical pound properties No. R₁ R₂ R₃ X B (mp ° C.) 4-1 Me Me H HPh 4-2 Me Me H H Ph(2-F) 114-116 4-3 Me Me H H Ph(2-Cl) 4-4 Me Me H HPh(2-OMe) 4-5 Me Me H H Ph(2,6-F₂) 170-172 4-6 Me Me H H Ph(2,6-Cl₂) 4-7Me Me H H Ph(2,6-OMe₂) 128-130 4-8 Me Me H 6-Cl Ph 4-9 Me Me H 6-ClPh(2-F) 4-10 Me Me H 6-Cl Ph(2-Cl) 4-11 Me Me H 6-Cl Ph(2,6-F₂) 4-12 MeMe H 6-Cl Ph(2,6-Cl₂) 4-13 Me Me H 6-Br Ph 4-14 Me Me H 6-Br Ph(2-F)4-15 Me Me H 6-Br Ph(2-Cl) 4-16 Me Me H 6-Br Ph(2,6-F₂) 4-17 Me Me H6-Br Ph(2,6-Cl₂) 4-18 Me Me H 6-CF₃ Ph(2,6-F₂) 4-19 Me Me H 6-CNPh(2,6-F₂) 4-20 Me CN H H Ph(2,6-F₂) 4-21 Me CO₂Et H H Ph(2,6-F₂) 4-22Me CN H 6-Cl Ph(2,6-F₂) 4-23 Me CO₂Et H 6-Cl Ph(2,6-F₂) 4-24 Me Et H HPh(2,6-F₂) 4-25 Me Me COMe H Ph(2,6-F₂) 4-26 Me Me CH₂OMe H Ph(2,6-F₂)4-27 Me Me H H 1-naphthyl 4-28 Me Me H H 2-naphthyl 4-29 Me Me H H2-thienyl 4-30 Me Me H H 3-thienyl 4-31 Me Me H H 2-pyrazinyl 4-32 Me MeH H 2-pyridyl 4-33 Me Me H H 3-pyridyl 4-34 Me Me H H 4-tri- 156-158fluorometh- yl-3-pyridyl 4-35 Me Me H H 4-pyridyl 4-36 Me Me H H 2-furyl4-37 Me Me H H 3-furyl 4-38 Me Me H 1-Cl Ph(2-F) 4-39 Me Me H 1-ClPh(2,6-F₂) 4-40 Me Me H 1-Cl Ph(2-Cl) 4-41 Me Me H 1-Cl Ph(2-Me) 4-42 MeMe H 1-Cl Ph(2-CF₃) 4-43 Me Me H 1-Cl Ph(2-F-6-Cl) 4-44 Me Me H 1-MePh(2-F) 4-45 Me Me H 1-Me Ph(2,6-F₂) 4-46 Me Me H 1-Me Ph(2-Cl) 4-47 MeMe H 1-Me Ph(2-Me) 4-48 Me Me H 1-Me Ph(2-CF3) 4-49 Me Me H 1-MePh(2-F-6-Cl) 4-50 Me Me H 3-Cl Ph(2-F) 4-51 Me Me H 3-Cl Ph(2,6-F₂) 4-52Me Me H 3-Cl Ph(2-Cl) 4-53 Me Me H 3-Cl Ph(2-Me) 4-54 Me Me H 3-ClPh(2-CF₃) 4-55 Me Me H 3-Cl Ph(2-F-6-Cl) 4-56 Me Me H 3-Me Ph(2-F) 4-57Me Me H 3-Me Ph(2,6-F₂) 4-58 Me Me H 3-Me Ph(2-Cl) 4-59 Me Me H 3-MePh(2-Me) 4-60 Me Me H 3-Me Ph(2-CF₃) 4-61 Me Me H 3-Me Ph(2-F-6-Cl) 4-62Me Me H 3-CF₃ Ph(2-F) 4-63 Me Me H 3-CF₃ Ph(2,6-F₂) 4-64 Me Me H 3-CF₃Ph(2-Cl) 4-65 Me Me H 3-CF₃ Ph(2-Me) 4-66 Me Me H 3-CF₃ Ph(2-CF₃) 4-67Me Me H 3-CF₃ Ph(2-F-6-Cl) 4-68 Me Me H 4-CF₃ Ph(2-F) 4-69 Me Me H 4-CF₃Ph(2,6-F₂) 4-70 Me Me H 4-CF₃ Ph(2-Cl) 4-71 Me Me H 4-CF₃ Ph(2-Me) 4-72Me Me H 4-CF₃ Ph(2-CF₃) 4-73 Me Me H 4-CF₃ Ph(2-F-6-Cl) 4-74 Me Me H3-CN Ph(2-F) 4-75 Me Me H 3-CN Ph(2,6-F₂) 4-76 Me Me H 3-CN Ph(2-Cl)4-77 Me Me H 3-CN Ph(2-Me) 4-78 Me Me H 3-CN Ph(2-CF₃) 4-79 Me Me H 3-CNPh(2-F-6-Cl) 4-80 Me Me H 4-CN Ph(2-F) 4-81 Me Me H 4-CN Ph(2,6-F₂) 4-82Me Me H 4-CN Ph(2-Cl) 4-83 Me Me H 4-CN Ph(2-Me) 4-84 Me Me H 4-CNPh(2-CF₃) 4-85 Me Me H 4-CN Ph(2-F-6-Cl)

TABLE 5

Physical properties Compound No. R₁ R₂ R₃ X B (mp ° C.) 5-1 Me Me H H Ph5-2 Me Me H H Ph(2-F) 5-3 Me Me H H Ph(2-Cl) 5-4 Me Me H H Ph(2-OMe) 5-5Me Me H H Ph(2,6-F₂) 108-110 5-6 Me Me H H Ph(2,6-Cl₂) 5-7 Me Me H HPh(2,6-OMe₂) 5-8 Me Me H 5-Cl Ph 5-9 Me Me H 5-Cl Ph(2-F) 127-130 5-10Me Me H 5-Cl Ph(2-Cl) 5-11 Me Me H 5-Cl Ph(2,6-F₂) 129-131 5-12 Me Me H5-Cl Ph(2,6-Cl₂) 5-13 Me Me H 5-Br Ph 5-14 Me Me H 5-Br Ph(2-F) 141-1425-15 Me Me H 5-Br Ph(2-Cl) 5-16 Me Me H 5-Br Ph(2,6-F₂) 145-147 5-17 MeMe H 5-Br Ph(2,6-Cl₂) 5-18 Me Me H 5-CF₃ Ph(2,6-F₂) 5-19 Me Me H 5-CNPh(2,6-F₂) 5-20 Me Me H 3-Me Ph(2,6-F₂) 124-127 5-21 Me CN H HPh(2,6-F₂) 5-22 Me CO₂Et H H Ph(2,6-F₂) 5-23 Me CN H 5-Cl Ph(2,6-F₂)5-24 Me CO₂Et H 5-Cl Ph(2,6-F₂) 5-25 Me Et H H Ph(2,6-F₂) 5-26 Me MeCOMe H Ph(2,6-F₂) 5-27 Me Me CH₂OMe H Ph(2,6-F₂) 5-28 Me Me H H1-naphthyl 5-29 Me Me H H 2-naphthyl 5-30 Me Me H H 2-thienyl 5-31 Me MeH H 3-thienyl 5-32 Me Me H H 2-pyrazinyl 5-33 Me Me H H 2-pyridyl 5-34Me Me H H 3-pyridyl 5-35 Me Me H H 4-trifluoro-methyl-3-pyridyl 5-36 MeMe H H 4-pyridyl 5-37 Me Me H H 2-furyl 5-38 Me Me H H 3-furyl 5-39 MeMe H 3-Br Ph(2,6-F₂) 5-40 Me Me H 3-CF₃ Ph(2,6-F₂) 5-41 Me Me H 3-CNPh(2,6-F₂) 5-42 Me Me H 5-Me Ph(2,6-F₂) 5-43 Me Me H 5-OSO₂CF₃ Ph(2-F)5-44 Me Me H 5-OSO₂CF₃ Ph(2,6-F₂) 5-45 Me Me H 5-OCH₂CF₃ Ph(2-F) 5-46 MeMe H 5-OCH₂CF₃ Ph(2,6-F₂) 5-47 Me Me H 3-Cl Ph(2-F) 5-48 Me Me H 3-ClPh(2,6-F₂) 5-49 Me Me H 3-Cl Ph(2-Cl) 5-50 Me Me H 3-Cl Ph(2-Me) 5-51 MeMe H 3-Cl Ph(2-CF₃) 5-52 Me Me H 3-Cl Ph(2-F-6-Cl) 5-53 Me Me H 4-ClPh(2-F) 5-54 Me Me H 4-Cl Ph(2,6-F₂) 5-55 Me Me H 4-Cl Ph(2-Cl) 5-56 MeMe H 4-Cl Ph(2-Me) 5-57 Me Me H 4-Cl Ph(2-CF₃) 5-58 Me Me H 4-ClPh(2-F-6-Cl) 5-59 Me Me H 3-Br Ph(2-F) 5-60 Me Me H 3-Br Ph(2,6-F₂) 5-61Me Me H 3-Br Ph(2-Cl) 5-62 Me Me H 3-Br Ph(2-Me) 5-63 Me Me H 3-BrPh(2-CF₃) 5-64 Me Me H 3-Br Ph(2-F-6-Cl) 5-65 Me Me H 4-Br Ph(2-F)120-123 5-66 Me Me H 4-Br Ph(2,6-F₂) 218-220 5-67 Me Me H 4-Br Ph(2-Cl)5-68 Me Me H 4-Br Ph(2-Me) 5-69 Me Me H 4-Br Ph(2-CF₃) 5-70 Me Me H 4-BrPh(2-F-6-Cl) 5-71 Me Me H 3-CF₃ Ph(2-F) 5-72 Me Me H 3-CF₃ Ph(2,6-F₂)5-73 Me Me H 3-CF₃ Ph(2-Cl) 5-74 Me Me H 3-CF₃ Ph(2-Me) 5-75 Me Me H3-CF₃ Ph(2-CF₃) 5-76 Me Me H 3-CF₃ Ph(2-F-6-Cl) 5-77 Me Me H 4-CF₃Ph(2-F) 5-78 Me Me H 4-CF₃ Ph(2,6-F₂) 5-79 Me Me H 4-CF₃ Ph(2-Cl) 5-80Me Me H 4-CF₃ Ph(2-Me) 5-81 Me Me H 4-CF₃ Ph(2-CF₃) 5-82 Me Me H 4-CF₃Ph(2-F-6-Cl) 5-83 Me Me H 5-CF₃ Ph(2-F) 5-84 Me Me H 5-CF₃ Ph(2-Cl) 5-85Me Me H 5-CF₃ Ph(2,6-Cl₂) 5-86 Me Me H 3-CN Ph(2-F) 5-87 Me Me H 3-CNPh(2,6-F₂) 5-88 Me Me H 3-CN Ph(2-Cl) 5-89 Me Me H 3-CN Ph(2-Me) 5-90 MeMe H 3-CN Ph(2-CF₃) 5-91 Me Me H 3-CN Ph(2-F-6-Cl) 5-92 Me Me H 4-CNPh(2-F) 5-93 Me Me H 4-CN Ph(2,6-F₂) 5-94 Me Me H 4-CN Ph(2-Cl) 5-95 MeMe H 4-CN Ph(2-Me) 5-96 Me Me H 4-CN Ph(2-CF₃) 5-97 Me Me H 4-CNPh(2-F-6-Cl) 5-98 Me Me H 5-CN Ph(2-F) 5-99 Me Me H 5-CN Ph(2-Cl) 5-100Me Me H 5-CN Ph(2,6-Cl₂) 5-101 Me Me H 3-OCF₃ Ph(2-F) 5-102 Me Me H3-OCF₃ Ph(2,6-F₂) 5-103 Me Me H 3-OCF₃ Ph(2-Cl) 5-104 Me Me H 3-OCF₃Ph(2-Me) 5-105 Me Me H 3-OCF₃ Ph(2-CF₃) 5-106 Me Me H 3-OCF₃Ph(2-F-6-Cl) 5-107 Me Me H 4-OCF₃ Ph(2-F) 5-108 Me Me H 4-OCF₃Ph(2,6-F₂) 5-109 Me Me H 4-OCF₃ Ph(2-Cl) 5-110 Me Me H 4-OCF₃ Ph(2-Me)5-111 Me Me H 4-OCF₃ Ph(2-CF₃) 5-112 Me Me H 4-OCF₃ Ph(2-F-6-Cl) 5-113Me Me H 5-OCF₃ Ph(2-F) 5-114 Me Me H 5-OCF₃ Ph(2,6-F₂) 5-115 Me Me H5-OCF₃ Ph(2-Cl) 5-116 Me Me H 5-OCF₃ Ph(2-Me) 5-117 Me Me H 5-OCF₃Ph(2-CF₃) 5-118 Me Me H 5-OCF₃ Ph(2-F-6-Cl) 5-119 Me Me H 3-OCHF₂Ph(2-F) 5-120 Me Me H 3-OCHF₂ Ph(2,6-F₂) 5-121 Me Me H 3-OCHF₂ Ph(2-Cl)5-122 Me Me H 3-OCHF₂ Ph(2-Me) 5-123 Me Me H 3-OCHF₂ Ph(2-CF₃) 5-124 MeMe H 3-OCHF₂ Ph(2-F-6-Cl) 5-125 Me Me H 4-OCHF₂ Ph(2-F) 5-126 Me Me H4-OCHF₂ Ph(2,6-F₂) 5-127 Me Me H 4-OCHF₂ Ph(2-Cl) 5-128 Me Me H 4-OCHF₂Ph(2-Me) 5-129 Me Me H 4-OCHF₂ Ph(2-CF₃) 5-130 Me Me H 4-OCHF₂Ph(2-F-6-Cl) 5-131 Me Me H 5-OCHF₂ Ph(2-F) 5-132 Me Me H 5-OCHF₂Ph(2,6-F₂) 5-133 Me Me H 5-OCHF₂ Ph(2-Cl) 5-134 Me Me H 5-OCHF₂ Ph(2-Me)5-135 Me Me H 5-OCHF₂ Ph(2-CF₃) 5-136 Me Me H 5-OCHF₂ Ph(2-F-6-Cl) 5-137Me Me H 3-OCH₂CF₃ Ph(2-F) 5-138 Me Me H 3-OCH₂CF₃ Ph(2,6-F₂) 5-139 Me MeH 3-OCH₂CF₃ Ph(2-Cl) 5-140 Me Me H 3-OCH₂CF₃ Ph(2-Me) 5-141 Me Me H3-OCH₂CF₃ Ph(2-CF₃) 5-142 Me Me H 3-OCH₂CF₃ Ph(2-F-6-Cl) 5-143 Me Me H4-OCH₂CF₃ Ph(2-F) 5-144 Me Me H 4-OCH₂CF₃ Ph(2,6-F₂) 5-145 Me Me H4-OCH₂CF₃ Ph(2-Cl) 5-146 Me Me H 4-OCH₂CF₃ Ph(2-Me) 5-147 Me Me H4-OCH₂CF₃ Ph(2-CF₃) 5-148 Me Me H 4-OCH₂CF₃ Ph(2-F-6-Cl) 5-149 Me Me H5-OCH₂CF₃ Ph(2-F) 5-150 Me Me H 5-OCH₂CF₃ Ph(2,6-F₂) 5-151 Me Me H5-OCH₂CF₃ Ph(2-Cl) 5-152 Me Me H 5-OCH₂CF₃ Ph(2-Me) 5-153 Me Me H5-OCH₂CF₃ Ph(2-CF₃) 5-154 Me Me H 5-OCH₂CF₃ Ph(2-F-6-Cl) 5-155 Me Me H5-Cl 4-trifluoromethyl-3-pyridyl 179-182 5-156 Me Me H 4,5-Br₂Ph(2,6-F₂) 128-130 5-157 Me Me H 4,5-Br₂ Ph(2-F) 173-175 5-158 Me Me H3-Me-4-Cl Ph(2-F) 5-159 Me Me H 3-Me-4-Cl Ph(2,6-F₂) 5-160 Me Me H3-Me-4-Cl Ph(2-Cl) 5-161 Me Me H 3-Me-4-Cl Ph(2-Me) 5-162 Me Me H3-Me-4-Cl Ph(2-CF₃) 5-163 Me Me H 3-Me-4-Cl Ph(2-F-6-Cl) 5-164 Me Me H3-Me-5-Cl Ph(2-F) 5-165 Me Me H 3-Me-5-Cl Ph(2,6-F₂) 5-166 Me Me H3-Me-5-Cl Ph(2-Cl) 5-167 Me Me H 3-Me-5-Cl Ph(2-Me) 5-168 Me Me H3-Me-5-Cl Ph(2-CF₃) 5-169 Me Me H 3-Me-5-Cl Ph(2-F-6-Cl) 5-170 Me Me H3-Me-4-Br Ph(2-F) 5-171 Me Me H 3-Me-4-Br Ph(2,6-F₂) 5-172 Me Me H3-Me-4-Br Ph(2-Cl) 5-173 Me Me H 3-Me-4-Br Ph(2-Me) 5-174 Me Me H3-Me-4-Br Ph(2-CF₃) 5-175 Me Me H 3-Me-4-Br Ph(2-F-6-Cl) 5-176 Me Me H3-Me-5-Br Ph(2-F) 5-177 Me Me H 3-Me-5-Br Ph(2,6-F₂) 5-178 Me Me H3-Me-5-Br Ph(2-Cl) 5-179 Me Me H 3-Me-5-Br Ph(2-Me) 5-180 Me Me H3-Me-5-Br Ph(2-CF₃) 5-181 Me Me H 3-Me-5-Br Ph(2-F-6-Cl) 5-182 Me Me H3-Me-4-CF₃ Ph(2-F) 5-183 Me Me H 3-Me-4-CF₃ Ph(2,6-F₂) 5-184 Me Me H3-Me-4-CF₃ Ph(2-Cl) 5-185 Me Me H 3-Me-4-CF₃ Ph(2-Me) 5-186 Me Me H3-Me-4-CF₃ Ph(2-CF₃) 5-187 Me Me H 3-Me-4-CF₃ Ph(2-F-6-Cl) 5-188 Me Me H3-Me-5-CF₃ Ph(2-F) 5-189 Me Me H 3-Me-5-CF₃ Ph(2,6-F₂) 5-190 Me Me H3-Me-5-CF₃ Ph(2-Cl) 5-191 Me Me H 3-Me-5-CF₃ Ph(2-Me) 5-192 Me Me H3-Me-5-CF₃ Ph(2-CF₃) 5-193 Me Me H 3-Me-5-CF₃ Ph(2-F-6-Cl) 5-194 Me Me H3-Me-4-OCF₃ Ph(2-F) 5-195 Me Me H 3-Me-4-OCF₃ Ph(2,6-F₂) 5-196 Me Me H3-Me-4-OCF₃ Ph(2-Cl) 5-197 Me Me H 3-Me-4-OCF₃ Ph(2-Me) 5-198 Me Me H3-Me-4-OCF₃ Ph(2-CF₃) 5-199 Me Me H 3-Me-4-OCF₃ Ph(2-F-6-Cl) 5-200 Me MeH 3-Me-5-OCF₃ Ph(2-F) 5-201 Me Me H 3-Me-5-OCF₃ Ph(2,6-F₂) 5-202 Me Me H3-Me-5-OCF₃ Ph(2-Cl) 5-203 Me Me H 3-Me-5-OCF₃ Ph(2-Me) 5-204 Me Me H3-Me-5-OCF₃ Ph(2-CF₃) 5-205 Me Me H 3-Me-5-OCF₃ Ph(2-F-6-Cl) 5-206 Me MeH 3-Me-4-OCHF₂ Ph(2-F) 5-207 Me Me H 3-Me-4-OCHF₂ Ph(2,6-F₂) 5-208 Me MeH 3-Me-4-OCHF₂ Ph(2-Cl) 5-209 Me Me H 3-Me-4-OCHF₂ Ph(2-Me) 5-210 Me MeH 3-Me-4-OCHF₂ Ph(2-CF₃) 5-211 Me Me H 3-Me-4-OCHF₂ Ph(2-F-6-Cl) 5-212Me Me H 3-Me-5-OCHF₂ Ph(2-F) 5-213 Me Me H 3-Me-5-OCHF₂ Ph(2,6-F₂) 5-214Me Me H 3-Me-5-OCHF₂ Ph(2-Cl) 5-215 Me Me H 3-Me-5-OCHF₂ Ph(2-Me) 5-216Me Me H 3-Me-5-OCHF₂ Ph(2-CF₃) 5-217 Me Me H 3-Me-5-OCHF₂ Ph(2-F-6-Cl)5-218 Me Me H 3-Me-4-OCH₂CF₃ Ph(2-F) 5-219 Me Me H 3-Me-4-OCH₂CF₃Ph(2,6-F₂) 5-220 Me Me H 3-Me-4-OCH₂CF₃ Ph(2-Cl) 5-221 Me Me H3-Me-4-OCH₂CF₃ Ph(2-Me) 5-222 Me Me H 3-Me-4-OCH₂CF₃ Ph(2-CF₃) 5-223 MeMe H 3-Me-4-OCH₂CF₃ Ph(2-F-6-Cl) 5-224 Me Me H 3-Me-5-OCH₂CF₃ Ph(2-F)5-225 Me Me H 3-Me-5-OCH₂CF₃ Ph(2,6-F₂) 5-226 Me Me H 3-Me-5-OCH₂CF₃Ph(2-Cl) 5-227 Me Me H 3-Me-5-OCH₂CF₃ Ph(2-Me) 5-228 Me Me H3-Me-5-OCH₂CF₃ Ph(2-CF₃) 5-229 Me Me H 3-Me-5-OCH₂CF₃ Ph(2-F-6-Cl) 5-230Me Me H 3,5-Cl₂ Ph(2-F) 5-231 Me Me H 3,5-Cl₂ Ph(2,6-F₂) 5-232 Me Me H3,5-Cl₂ Ph(2-Cl) 5-233 Me Me H 3,5-Cl₂ Ph(2-Me) 5-234 Me Me H 3,5-Cl₂Ph(2-CF₃) 5-235 Me Me H 3,5-Cl₂ Ph(2-F-6-Cl) 5-236 Me Me H 3-Cl-5-BrPh(2-F) 5-237 Me Me H 3-Cl-5-Br Ph(2,6-F₂) 5-238 Me Me H 3-Cl-5-BrPh(2-Cl) 5-239 Me Me H 3-Cl-5-Br Ph(2-Me) 5-240 Me Me H 3-Cl-5-BrPh(2-CF₃) 5-241 Me Me H 3-Cl-5-Br Ph(2-F-6-Cl) 5-242 Me Me H 3-Cl-5-CF₃Ph(2-F) 5-243 Me Me H 3-Cl-5-CF₃ Ph(2,6-F₂) 5-244 Me Me H 3-Cl-5-CF₃Ph(2-Cl) 5-245 Me Me H 3-Cl-5-CF₃ Ph(2-Me) 5-246 Me Me H 3-Cl-5-CF₃Ph(2-CF₃) 5-247 Me Me H 3-Cl-5-CF₃ Ph(2-F-6-Cl) 5-248 Me Me H3-Cl-5-OCF₃ Ph(2-F) 5-249 Me Me H 3-Cl-5-OCF₃ Ph(2,6-F₂) 5-250 Me Me H3-Cl-5-OCF₃ Ph(2-Cl) 5-251 Me Me H 3-Cl-5-OCF₃ Ph(2-Me) 5-252 Me Me H3-Cl-5-OCF₃ Ph(2-CF₃) 5-253 Me Me H 3-Cl-5-OCF₃ Ph(2-F-6-Cl) 5-254 Me MeH 3-Cl-5-OCHF₂ Ph(2-F) 5-255 Me Me H 3-Cl-5-OCHF₂ Ph(2,6-F₂) 5-256 Me MeH 3-Cl-5-OCHF₂ Ph(2-Cl) 5-257 Me Me H 3-Cl-5-OCHF₂ Ph(2-Me) 5-258 Me MeH 3-Cl-5-OCHF₂ Ph(2-CF₃) 5-259 Me Me H 3-Cl-5-OCHF₂ Ph(2-F-6-Cl) 5-260Me Me H 3-Cl-5-OCH₂CF₃ Ph(2-F) 5-261 Me Me H 3-Cl-5-OCH₂CF₃ Ph(2,6-F₂)5-262 Me Me H 3-Cl-5-OCH₂CF₃ Ph(2-Cl) 5-263 Me Me H 3-Cl-5-OCH₂CF₃Ph(2-Me) 5-264 Me Me H 3-Cl-5-OCH₂CF₃ Ph(2-CF₃) 5-265 Me Me H3-Cl-5-OCH₂CF₃ Ph(2-F-6-Cl)

TABLE 6

Physical properties Compound No. R₁ R₂ R₃ X B (mp ° C.) 6-1 Me Me H H Ph6-2 Me Me H H Ph(2-F) 6-3 Me Me H H Ph(2-Cl) 6-4 Me Me H H Ph(2-OMe) 6-5Me Me H H Ph(2,6-F₂) 139-142 6-6 Me Me H H Ph(2,6-Cl₂) 6-7 Me Me H HPh(2,6-OMe₂) 6-8 Me Me H 2-Cl Ph 6-9 Me Me H 2-Cl Ph(2-F) 6-10 Me Me H2-Cl Ph(2-Cl) 6-11 Me Me H 2-Cl Ph(2,6-F₂) 6-12 Me Me H 2-Cl Ph(2,6-Cl₂)6-13 Me Me H 2-Br Ph 6-14 Me Me H 2-Br Ph(2-F) 6-15 Me Me H 2-BrPh(2-Cl) 6-16 Me Me H 2-Br Ph(2,6-F₂) 6-17 Me Me H 2-Br Ph(2,6-Cl₂) 6-18Me Me H 2-CF₃ Ph(2,6-F₂) 6-19 Me Me H 2-CN Ph(2,6-F₂) 6-20 Me CN H HPh(2,6-F₂) 6-21 Me CO₂Et H H Ph(2,6-F₂) 6-22 Me CN H 2-Cl Ph(2,6-F₂)6-23 Me CO₂Et H 2-Cl Ph(2,6-F₂) 6-24 Me Et H H Ph(2,6-F₂) 6-25 Me MeCOMe H Ph(2,6-F₂) 6-26 Me Me CH₂OMe H Ph(2,6-F₂) 6-27 Me Me H H1-naphthyl 6-28 Me Me H H 2-naphthyl 6-29 Me Me H H 2-thienyl 6-30 Me MeH H 3-thienyl 6-31 Me Me H H 2-pyrazinyl 6-32 Me Me H H 2-pyridyl 6-33Me Me H H 3-pyridyl 6-34 Me Me H H 4-trifluoro- methyl-3-pyridyl 6-35 MeMe H H 4-pyridyl 6-36 Me Me H H 2-furyl 6-37 Me Me H H 3-furyl 6-38 MeMe H 4-Cl Ph(2-F) 6-39 Me Me H 4-Cl Ph(2,6-F₂) 6-40 Me Me H 4-ClPh(2-Cl) 6-41 Me Me H 4-Cl Ph(2-Me) 6-42 Me Me H 4-Cl Ph(2-CF₃) 6-43 MeMe H 4-Cl Ph(2-F-6-Cl) 6-44 Me Me H 5-Cl Ph(2-F) 6-45 Me Me H 5-ClPh(2,6-F₂) 6-46 Me Me H 5-Cl Ph(2-Cl) 6-47 Me Me H 5-Cl Ph(2-Me) 6-48 MeMe H 5-Cl Ph(2-CF₃) 6-49 Me Me H 5-Cl Ph(2-F-6-Cl) 6-50 Me Me H 5-BrPh(2-F) 6-51 Me Me H 5-Br Ph(2,6-F₂) 6-52 Me Me H 5-Br Ph(2-Cl) 6-53 MeMe H 5-Br Ph(2-Me) 6-54 Me Me H 5-Br Ph(2-CF₃) 6-55 Me Me H 5-BrPh(2-F-6-Cl) 6-56 Me Me H 2-Me Ph(2-F) 6-57 Me Me H 2-Me Ph(2,6-F₂) 6-58Me Me H 2-Me Ph(2-Cl) 6-59 Me Me H 2-Me Ph(2-Me) 6-60 Me Me H 2-MePh(2-CF₃) 6-61 Me Me H 2-Me Ph(2-F-6-Cl) 6-62 Me Me H 4-Me Ph(2-F) 6-63Me Me H 4-Me Ph(2,6-F₂) 6-64 Me Me H 4-Me Ph(2-Cl) 6-65 Me Me H 4-MePh(2-Me) 6-66 Me Me H 4-Me Ph(2-CF₃) 6-67 Me Me H 4-Me Ph(2-F-6-Cl) 6-68Me Me H 5-CF₃ Ph(2-F) 6-69 Me Me H 5-CF₃ Ph(2,6-F₂) 6-70 Me Me H 5-CF₃Ph(2-Cl) 6-71 Me Me H 5-CF₃ Ph(2-Me) 6-72 Me Me H 5-CF₃ Ph(2-CF₃) 6-73Me Me H 5-CF₃ Ph(2-F-6-Cl) 6-74 Me Me H 5-OCF₃ Ph(2-F) 6-75 Me Me H5-OCF₃ Ph(2,6-F₂) 6-76 Me Me H 5-OCF₃ Ph(2-Cl) 6-77 Me Me H 5-OCF₃Ph(2-Me) 6-78 Me Me H 5-OCF₃ Ph(2-CF₃) 6-79 Me Me H 5-OCF₃ Ph(2-F-6-Cl)6-80 Me Me H 5-OCHF₂ Ph(2-F) 6-81 Me Me H 5-OCHF₂ Ph(2,6-F₂) 6-82 Me MeH 5-OCHF₂ Ph(2-Cl) 6-83 Me Me H 5-OCHF₂ Ph(2-Me) 6-84 Me Me H 5-OCHF₂Ph(2-CF₃) 6-85 Me Me H 5-OCHF₂ Ph(2-F-6-Cl) 6-86 Me Me H 5-OCH₂CF₃Ph(2-F) 6-87 Me Me H 5-OCH₂CF₃ Ph(2,6-F₂) 6-88 Me Me H 5-OCH₂CF₃Ph(2-Cl) 6-89 Me Me H 5-OCH₂CF₃ Ph(2-Me) 6-90 Me Me H 5-OCH₂CF₃Ph(2-CF₃) 6-91 Me Me H 5-OCH₂CF₃ Ph(2-F-6-Cl) 6-92 Me Me H 2,5-Cl₂Ph(2-F) 6-93 Me Me H 2,5-Cl₂ Ph(2,6-F₂) 6-94 Me Me H 2,5-Cl₂ Ph(2-Cl)6-95 Me Me H 2,5-Cl₂ Ph(2-Me) 6-96 Me Me H 2,5-Cl₂ Ph(2-CF₃) 6-97 Me MeH 2,5-Cl₂ Ph(2-F-6-Cl) 6-98 Me Me H 4,5-Cl₂ Ph(2-F) 6-99 Me Me H 4,5-Cl₂Ph(2,6-F₂) 6-100 Me Me H 4,5-Cl₂ Ph(2-Cl) 6-101 Me Me H 4,5-Cl₂ Ph(2-Me)6-102 Me Me H 4,5-Cl₂ Ph(2-CF₃) 6-103 Me Me H 4,5-Cl₂ Ph(2-F-6-Cl) 6-104Me Me H 2-Cl-5-Br Ph(2-F) 6-105 Me Me H 2-Cl-5-Br Ph(2,6-F₂) 6-106 Me MeH 2-Cl-5-Br Ph(2-Cl) 6-107 Me Me H 2-Cl-5-Br Ph(2-Me) 6-108 Me Me H2-Cl-5-Br Ph(2-CF₃) 6-109 Me Me H 2-Cl-5-Br Ph(2-F-6-Cl) 6-110 Me Me H4-Cl-5-Br Ph(2-F) 6-111 Me Me H 4-Cl-5-Br Ph(2,6-F₂) 6-112 Me Me H4-Cl-5-Br Ph(2-Cl) 6-113 Me Me H 4-Cl-5-Br Ph(2-Me) 6-114 Me Me H4-Cl-5-Br Ph(2-CF₃) 6-115 Me Me H 4-Cl-5-Br Ph(2-F-6-Cl) 6-116 Me Me H2-Cl-5-CF₃ Ph(2-F) 6-117 Me Me H 2-Cl-5-CF₃ Ph(2,6-F₂) 6-118 Me Me H2-Cl-5-CF₃ Ph(2-Cl) 6-119 Me Me H 2-Cl-5-CF₃ Ph(2-Me) 6-120 Me Me H2-Cl-5-CF₃ Ph(2-CF₃) 6-121 Me Me H 2-Cl-5-CF₃ Ph(2-F-6-Cl) 6-122 Me Me H4-Cl-5-CF₃ Ph(2-F) 6-123 Me Me H 4-Cl-5-CF₃ Ph(2,6-F₂) 6-124 Me Me H4-Cl-5-CF₃ Ph(2-Cl) 6-125 Me Me H 4-Cl-5-CF₃ Ph(2-Me) 6-126 Me Me H4-Cl-5-CF₃ Ph(2-CF₃) 6-127 Me Me H 4-Cl-5-CF₃ Ph(2-F-6-Cl) 6-128 Me Me H2-Cl-5-OCF₃ Ph(2-F) 6-129 Me Me H 2-Cl-5-OCF₃ Ph(2,6-F₂) 6-130 Me Me H2-Cl-5-OCF₃ Ph(2-Cl) 6-131 Me Me H 2-Cl-5-OCF₃ Ph(2-Me) 6-132 Me Me H2-Cl-5-OCF₃ Ph(2-CF₃) 6-133 Me Me H 2-Cl-5-OCF₃ Ph(2-F-6-Cl) 6-134 Me MeH 4-Cl-5-OCF₃ Ph(2-F) 6-135 Me Me H 4-Cl-5-OCF₃ Ph(2,6-F₂) 6-136 Me Me H4-Cl-5-OCF₃ Ph(2-Cl) 6-137 Me Me H 4-Cl-5-OCF₃ Ph(2-Me) 6-138 Me Me H4-Cl-5-OCF₃ Ph(2-CF₃) 6-139 Me Me H 4-Cl-5-OCF₃ Ph(2-F-6-Cl) 6-140 Me MeH 2-Cl-5-OCHF₂ Ph(2-F) 6-141 Me Me H 2-Cl-5-OCHF₂ Ph(2,6-F₂) 6-142 Me MeH 2-Cl-5-OCHF₂ Ph(2-Cl) 6-143 Me Me H 2-Cl-5-OCHF₂ Ph(2-Me) 6-144 Me MeH 2-Cl-5-OCHF₂ Ph(2-CF₃) 6-145 Me Me H 2-Cl-5-OCHF₂ Ph(2-F-6-Cl) 6-146Me Me H 4-Cl-5-OCHF₂ Ph(2-F) 6-147 Me Me H 4-Cl-5-OCHF₂ Ph(2,6-F₂) 6-148Me Me H 4-Cl-5-OCHF₂ Ph(2-Cl) 6-149 Me Me H 4-Cl-5-OCHF₂ Ph(2-Me) 6-150Me Me H 4-Cl-5-OCHF₂ Ph(2-CF₃) 6-151 Me Me H 4-Cl-5-OCHF₂ Ph(2-F-6-Cl)6-152 Me Me H 2-Cl-5-OCH₂CF₃ Ph(2-F) 6-153 Me Me H 2-Cl-5-OCH₂CF₃Ph(2,6-F₂) 6-154 Me Me H 2-Cl-5-OCH₂CF₃ Ph(2-Cl) 6-155 Me Me H2-Cl-5-OCH₂CF₃ Ph(2-Me) 6-156 Me Me H 2-Cl-5-OCH₂CF₃ Ph(2-CF₃) 6-157 MeMe H 2-Cl-5-OCH₂CF₃ Ph(2-F-6-Cl) 6-158 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2-F)6-159 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2,6-F₂) 6-160 Me Me H 4-Cl-5-OCH₂CF₃Ph(2-Cl) 6-161 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2-Me) 6-162 Me Me H4-Cl-5-OCH₂CF₃ Ph(2-CF₃) 6-163 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2-F-6-Cl) 6-164Me Me H 2-Me-5-Cl Ph(2-F) 6-165 Me Me H 2-Me-5-Cl Ph(2,6-F₂) 6-166 Me MeH 2-Me-5-Cl Ph(2-Cl) 6-167 Me Me H 2-Me-5-Cl Ph(2-Me) 6-168 Me Me H2-Me-5-Cl Ph(2-CF₃) 6-169 Me Me H 2-Me-5-Cl Ph(2-F-6-Cl) 6-170 Me Me H4-Me-5-Cl Ph(2-F) 6-171 Me Me H 4-Me-5-Cl Ph(2,6-F₂) 6-172 Me Me H4-Me-5-Cl Ph(2-Cl) 6-173 Me Me H 4-Me-5-Cl Ph(2-Me) 6-174 Me Me H4-Me-5-Cl Ph(2-CF₃) 6-175 Me Me H 4-Me-5-Cl Ph(2-F-6-Cl) 6-176 Me Me H2-Me-5-Br Ph(2-F) 6-177 Me Me H 2-Me-5-Br Ph(2,6-F₂) 6-178 Me Me H2-Me-5-Br Ph(2-Cl) 6-179 Me Me H 2-Me-5-Br Ph(2-Me) 6-180 Me Me H2-Me-5-Br Ph(2-CF₃) 6-181 Me Me H 2-Me-5-Br Ph(2-F-6-Cl) 6-182 Me Me H4-Me-5-Br Ph(2-F) 6-183 Me Me H 4-Me-5-Br Ph(2,6-F₂) 6-184 Me Me H4-Me-5-Br Ph(2-Cl) 6-185 Me Me H 4-Me-5-Br Ph(2-Me) 6-186 Me Me H4-Me-5-Br Ph(2-CF₃) 6-187 Me Me H 4-Me-5-Br Ph(2-F-6-Cl) 6-188 Me Me H2-Me-5-CF₃ Ph(2-F) 6-189 Me Me H 2-Me-5-CF₃ Ph(2,6-F₂) 6-190 Me Me H2-Me-5-CF₃ Ph(2-Cl) 6-191 Me Me H 2-Me-5-CF₃ Ph(2-Me) 6-192 Me Me H2-Me-5-CF₃ Ph(2-CF₃) 6-193 Me Me H 2-Me-5-CF₃ Ph(2-F-6-Cl) 6-194 Me Me H4-Me-5-CF₃ Ph(2-F) 6-195 Me Me H 4-Me-5-CF₃ Ph(2,6-F₂) 6-196 Me Me H4-Me-5-CF₃ Ph(2-Cl) 6-197 Me Me H 4-Me-5-CF₃ Ph(2-Me) 6-198 Me Me H4-Me-5-CF₃ Ph(2-CF₃) 6-199 Me Me H 4-Me-5-CF₃ Ph(2-F-6-Cl) 6-200 Me Me H2-Me-5-OCF₃ Ph(2-F) 6-201 Me Me H 2-Me-5-OCF₃ Ph(2,6-F₂) 6-202 Me Me H2-Me-5-OCF₃ Ph(2-Cl) 6-203 Me Me H 2-Me-5-OCF₃ Ph(2-Me) 6-204 Me Me H2-Me-5-OCF₃ Ph(2-CF₃) 6-205 Me Me H 2-Me-5-OCF₃ Ph(2-F-6-Cl) 6-206 Me MeH 4-Me-5-OCF₃ Ph(2-F) 6-207 Me Me H 4-Me-5-OCF₃ Ph(2,6-F₂) 6-208 Me Me H4-Me-5-OCF₃ Ph(2-Cl) 6-209 Me Me H 4-Me-5-OCF₃ Ph(2-Me) 6-210 Me Me H4-Me-5-OCF₃ Ph(2-CF₃) 6-211 Me Me H 4-Me-5-OCF₃ Ph(2-F-6-Cl) 6-212 Me MeH 2-Me-5-OCHF₂ Ph(2-F) 6-213 Me Me H 2-Me-5-OCHF₂ Ph(2,6-F₂) 6-214 Me MeH 2-Me-5-OCHF₂ Ph(2-Cl) 6-215 Me Me H 2-Me-5-OCHF₂ Ph(2-Me) 6-216 Me MeH 2-Me-5-OCHF₂ Ph(2-CF₃) 6-217 Me Me H 2-Me-5-OCHF₂ Ph(2-F-6-Cl) 6-218Me Me H 4-Me-5-OCHF₂ Ph(2-F) 6-219 Me Me H 4-Me-5-OCHF₂ Ph(2,6-F₂) 6-220Me Me H 4-Me-5-OCHF₂ Ph(2-Cl) 6-221 Me Me H 4-Me-5-OCHF₂ Ph(2-Me) 6-222Me Me H 4-Me-5-OCHF₂ Ph(2-CF₃) 6-223 Me Me H 4-Me-5-OCHF₂ Ph(2-F-6-Cl)6-224 Me Me H 2-Me-5-OCH₂CF₃ Ph(2-F) 6-225 Me Me H 2-Me-5-OCH₂CF₃Ph(2,6-F₂) 6-226 Me Me H 2-Me-5-OCH₂CF₃ Ph(2-Cl) 6-227 Me Me H2-Me-5-OCH₂CF₃ Ph(2-Me) 6-228 Me Me H 2-Me-5-OCH₂CF₃ Ph(2-CF₃) 6-229 MeMe H 2-Me-5-OCH₂CF₃ Ph(2-F-6-Cl) 6-230 Me Me H 4-Me-5-OCH₂CF₃ Ph(2-F)6-231 Me Me H 4-Me-5-OCH₂CF₃ Ph(2,6-F₂) 6-232 Me Me H 4-Me-5-OCH₂CF₃Ph(2-Cl) 6-233 Me Me H 4-Me-5-OCH₂CF₃ Ph(2-Me) 6-234 Me Me H4-Me-5-OCH₂CF₃ Ph(2-CF₃) 6-235 Me Me H 4-Me-5-OCH₂CF₃ Ph(2-F-6-Cl)

TABLE 7

Physical properties Compound No. R₁ R₂ R₃ X₁ X₂ X₃ B (mp ° C.) 7-1 Me MeH Me Me Me Ph(2-Cl) 7-2 Me Me H Me Me Me Ph(4-Cl) 7-3 Me Me H Me Me MePh(2-CF₃) 7-4 Me Me H Me Me Me Ph(4-CF₃) 7-5 Me Me H Me Me Me Ph(2-F)7-6 Me Me H Me Me Me Ph(2,6-F₂) 7-7 Me Me H Me Me Me Ph(2,6-(OMe)₂) 7-8Me Me H Cl Cl Me Ph(2-Cl) 7-9 Me Me H Cl Cl Me Ph(4-Cl) 7-10 Me Me H ClCl Me Ph(2-CF₃) 7-11 Me Me H Cl Cl Me Ph(4-CF₃) 7-12 Me Me H Cl Cl MePh(2-F) 7-13 Me Me H Cl Cl Me Ph(2,6-F₂) 7-14 Me Me H Cl Me Me Ph(2-Cl)7-15 Me Me H Cl Me Me Ph(4-Cl) 7-16 Me Me H Cl Me Me Ph(2-CF₃) 7-17 MeMe H Cl Me Me Ph(4-CF₃) 7-18 Me Me H Cl Me Me Ph(2-F) 7-19 Me Me H Cl MeMe Ph(2,6-F₂) 7-20 Me Me H Cl CF₃ Me Ph(2-Cl) 7-21 Me Me H Cl CF₃ MePh(4-Cl) 7-22 Me Me H Cl CF₃ Me Ph(2-CF₃) 7-23 Me Me H Cl CF₃ MePh(4-CF₃) 7-24 Me Me H Cl CF₃ Me Ph(2-F) 7-25 Me Me H Cl CF₃ MePh(2,6-F₂) 7-26 Me Me H Me H Me Ph(2-F) 7-27 Me Me H Me H Me Ph(2,6-F₂)7-28 Me Me H Me H Me Ph(2-Cl) 7-29 Me Me H Me H Me Ph(2-Me) 7-30 Me Me HMe H Me Ph(2-CF₃) 7-31 Me Me H Me H Me Ph(2-F-6-Cl) 7-32 Me Me H H Me MePh(2-F) 7-33 Me Me H H Me Me Ph(2,6-F₂) 7-34 Me Me H H Me Me Ph(2-Cl)7-35 Me Me H H Me Me Ph(2-Me) 7-36 Me Me H H Me Me Ph(2-CF₃) 7-37 Me MeH H Me Me Ph(2-F-6-Cl) 7-38 Me Me H H H H Ph(2-F) 7-39 Me Me H H H HPh(2,6-F₂) 7-40 Me Me H H H H Ph(2-Cl) 7-41 Me Me H H H H Ph(2-Me) 7-42Me Me H H H H Ph(2-CF₃) 7-43 Me Me H H H H Ph(2-F-6-Cl) 7-44 Me Me H MeH H Ph(2-F) 7-45 Me Me H Me H H Ph(2,6-F₂) 7-46 Me Me H Me H H Ph(2-Cl)7-47 Me Me H Me H H Ph(2-Me) 7-48 Me Me H Me H H Ph(2-CF₃) 7-49 Me Me HMe H H Ph(2-F-6-Cl) 7-50 Me Me H Cl H H Ph(2-F) 7-51 Me Me H Cl H HPh(2,6-F₂) 7-52 Me Me H Cl H H Ph(2-Cl) 7-53 Me Me H Cl H H Ph(2-Me)7-54 Me Me H Cl H H Ph(2-CF₃) 7-55 Me Me H Cl H H Ph(2-F-6-Cl) 7-56 MeMe H H Me H Ph(2-F) 7-57 Me Me H H Me H Ph(2,6-F₂) 7-58 Me Me H H Me HPh(2-Cl) 7-59 Me Me H H Me H Ph(2-Me) 7-60 Me Me H H Me H Ph(2-CF₃) 7-61Me Me H H Me H Ph(2-F-6-Cl) 7-62 Me Me H H Cl H Ph(2-F) 7-63 Me Me H HCl H Ph(2,6-F₂) 7-64 Me Me H H Cl H Ph(2-Cl) 7-65 Me Me H H Cl HPh(2-Me) 7-66 Me Me H H Cl H Ph(2-CF₃) 7-67 Me Me H H Cl H Ph(2-F-6-Cl)7-68 Me Me H H H Et Ph(2-F) 7-69 Me Me H H H Et Ph(2,6-F₂) 7-70 Me Me HH H Et Ph(2-Cl) 7-71 Me Me H H H Et Ph(2-Me) 7-72 Me Me H H H EtPh(2-CF₃) 7-73 Me Me H H H Et Ph(2-F-6-Cl) 7-74 Me Me H Me H Et Ph(2-F)7-75 Me Me H Me H Et Ph(2,6-F₂) 7-76 Me Me H Me H Et Ph(2-Cl) 7-77 Me MeH Me H Et Ph(2-Me) 7-78 Me Me H Me H Et Ph(2-CF₃) 7-79 Me Me H Me H EtPh(2-F-6-Cl) 7-80 Me Me H Cl H Et Ph(2-F) 7-81 Me Me H Cl H EtPh(2,6-F₂) 7-82 Me Me H Cl H Et Ph(2-Cl) 7-83 Me Me H Cl H Et Ph(2-Me)7-84 Me Me H Cl H Et Ph(2-CF₃) 7-85 Me Me H Cl H Et Ph(2-F-6-Cl) 7-86 MeMe H H Me Et Ph(2-F) 7-87 Me Me H H Me Et Ph(2,6-F₂) 7-88 Me Me H H MeEt Ph(2-Cl) 7-89 Me Me H H Me Et Ph(2-Me) 7-90 Me Me H H Me Et Ph(2-CF₃)7-91 Me Me H H Me Et Ph(2-F-6-Cl) 7-92 Me Me H H Cl Et Ph(2-F) 7-93 MeMe H H Cl Et Ph(2,6-F₂) 7-94 Me Me H H Cl Et Ph(2-Cl) 7-95 Me Me H H ClEt Ph(2-Me) 7-96 Me Me H H Cl Et Ph(2-CF₃) 7-97 Me Me H H Cl EtPh(2-F-6-Cl) 7-98 Me Me H H H Ph Ph(2-F) 7-99 Me Me H H H Ph Ph(2,6-F₂)7-100 Me Me H H H Ph Ph(2-Cl) 7-101 Me Me H H H Ph Ph(2-Me) 7-102 Me MeH H H Ph Ph(2-CF₃) 7-103 Me Me H H H Ph Ph(2-F-6-Cl) 7-104 Me Me H Me HPh Ph(2-F) 7-105 Me Me H Me H Ph Ph(2,6-F₂) 7-106 Me Me H Me H PhPh(2-Cl) 7-107 Me Me H Me H Ph Ph(2-Me) 7-108 Me Me H Me H Ph Ph(2-CF₃)7-109 Me Me H Me H Ph Ph(2-F-6-Cl) 7-110 Me Me H Cl H Ph Ph(2-F) 7-111Me Me H Cl H Ph Ph(2,6-F₂) 7-112 Me Me H Cl H Ph Ph(2-Cl) 7-113 Me Me HCl H Ph Ph(2-Me) 7-114 Me Me H Cl H Ph Ph(2-CF₃) 7-115 Me Me H Cl H PhPh(2-F-6-Cl) 7-116 Me Me H H Me Ph Ph(2-F) 7-117 Me Me H H Me PhPh(2,6-F₂) 7-118 Me Me H H Me Ph Ph(2-Cl) 7-119 Me Me H H Me Ph Ph(2-Me)7-120 Me Me H H Me Ph Ph(2-CF₃) 7-121 Me Me H H Me Ph Ph(2-F-6-Cl) 7-122Me Me H H Cl Ph Ph(2-F) 7-123 Me Me H H Cl Ph Ph(2-6-F₂) 7-124 Me Me H HCl Ph Ph(2-Cl) 7-125 Me Me H H Cl Ph Ph(2-Me) 7-126 Me Me H H Cl PhPh(2-CF₃) 7-127 Me Me H H Cl Ph Ph(2-F-6-Cl) 7-128 Me Me H H H Ph(4-Cl)Ph(2-F) 7-129 Me Me H H H Ph(4-Cl) Ph(2,6-F₂) 7-130 Me Me H H H Ph(4-Cl)Ph(2-Cl) 7-131 Me Me H H H Ph(4-C1) Ph(2-Me) 7-132 Me Me H H H Ph(4-Cl)Ph(2-CF₃) 7-133 Me Me H H H Ph(4-Cl) Ph(2-F-6-Cl) 7-134 Me Me H Me HPh(4-Cl) Ph(2-F) 7-135 Me Me H Me H Ph(4-Cl) Ph(2,6-F₂) 7-136 Me Me H MeH Ph(4-Cl) Ph(2-Cl) 7-137 Me Me H Me H Ph(4-Cl) Ph(2-Me) 7-138 Me Me HMe H Ph(4-Cl) Ph(2-CF₃) 7-139 Me Me H Me H Ph(4-Cl) Ph(2-F-6-Cl) 7-140Me Me H Cl H Ph(4-Cl) Ph(2-F) 7-141 Me Me H Cl H Ph(4-Cl) Ph(2,6-F₂)7-142 Me Me H Cl H Ph(4-Cl) Ph(2-Cl) 7-143 Me Me H Cl H Ph(4-Cl)Ph(2-Me) 7-144 Me Me H Cl H Ph(4-Cl) Ph(2-CF₃) 7-145 Me Me H Cl HPh(4-Cl) Ph(2-F-6-Cl) 7-146 Me Me H H Me Ph(4-Cl) Ph(2-F) 7-147 Me Me HH Me Ph(4-Cl) Ph(2,6-F₂) 7-148 Me Me H H Me Ph(4-Cl) Ph(2-Cl) 7-149 MeMe H H Me Ph(4-Cl) Ph(2-Me) 7-150 Me Me H H Me Ph(4-Cl) Ph(2-CF₃) 7-151Me Me H H Me Ph(4-Cl) Ph(2-F-6-Cl) 7-152 Me Me H H Cl Ph(4-Cl) Ph(2-F)7-153 Me Me H H Cl Ph(4-Cl) Ph(2,6-F₂) 7-154 Me Me H H Cl Ph(4-Cl)Ph(2-Cl) 7-155 Me Me H H Cl Ph(4-Cl) Ph(2-Me) 7-156 Me Me H H ClPh(4-Cl) Ph(2-CF₃) 7-157 Me Me H H Cl Ph(4-Cl) Ph(2-F-6-Cl) 7-158 Me MeH H H Ph(4-CF₃) Ph(2-F) 7-159 Me Me H H H Ph(4-CF₃) Ph(2,6-F₂) 7-160 MeMe H H H Ph(4-CF₃) Ph(2-Cl) 7-161 Me Me H H H Ph(4-CF₃) Ph(2-Me) 7-162Me Me H H H Ph(4-CF₃) Ph(2-CF₃) 7-163 Me Me H H H Ph(4-CF₃) Ph(2-F-6-Cl)7-164 Me Me H Me H Ph(4-CF₃) Ph(2-F) 7-165 Me Me H Me H Ph(4-CF₃)Ph(2,6-F₂) 7-166 Me Me H Me H Ph(4-CF₃) Ph(2-Cl) 7-167 Me Me H Me HPh(4-CF₃) Ph(2-Me) 7-168 Me Me H Me H Ph(4-CF₃) Ph(2-CF₃) 7-169 Me Me HMe H Ph(4-CF₃) Ph(2-F-6-Cl) 7-170 Me Me H Cl H Ph(4-CF₃) Ph(2-F) 7-171Me Me H Cl H Ph(4-CF₃) Ph(2,6-F₂) 7-172 Me Me H Cl H Ph(4-CF₃) Ph(2-Cl)7-173 Me Me H Cl H Ph(4-CF₃) Ph(2-Me) 7-174 Me Me H Cl H Ph(4-CF₃)Ph(2-CF₃) 7-175 Me Me H Cl H Ph(4-CF₃) Ph(2-F-6-Cl) 7-176 Me Me H H MePh(4-CF₃) Ph(2-F) 7-177 Me Me H H Me Ph(4-CF₃) Ph(2,6-F₂) 7-178 Me Me HH Me Ph(4-CF₃) Ph(2-Cl) 7-179 Me Me H H Me Ph(4-CF₃) Ph(2-Me) 7-180 MeMe H H Me Ph(4-CF₃) Ph(2-CF₃) 7-181 Me Me H H Me Ph(4-CF₃) Ph(2-F-6-Cl)7-182 Me Me H H Cl Ph(4-CF₃) Ph(2-F) 7-183 Me Me H H Cl Ph(4-CF₃)Ph(2,6-F₂) 7-184 Me Me H H Cl Ph(4-CF₃) Ph(2-Cl) 7-185 Me Me H H ClPh(4-CF₃) Ph(2-Me) 7-186 Me Me H H Cl Ph(4-CF₃) Ph(2-CF₃) 7-187 Me Me HH Cl Ph(4-CF₃) Ph(2-F-6-Cl)

TABLE 8

Physical properties Compound No. R₁ R₂ R₃ X B (mp ° C.) 8-1 Me Me H H Ph8-2 Me Me H H Ph(2-F) 44-45 8-3 Me Me H H Ph(2-Cl) 8-4 Me Me H HPh(2-OMe) 8-5 Me Me H H Ph(2,6-F₂) 112-114 8-6 Me Me H H Ph(2,6-Cl₂) 8-7Me Me H H Ph(2,6-OMe₂) 8-8 Me Me H 6-Cl Ph 8-9 Me Me H 6-Cl Ph(2-F) 8-10Me Me H 6-Cl Ph(2-Cl) 8-11 Me Me H 6-Cl Ph(2,6-F₂) 8-12 Me Me H 6-ClPh(2,6-Cl₂) 8-13 Me Me H 6-Br Ph 8-14 Me Me H 6-Br Ph(2-F) 8-15 Me Me H6-Br Ph(2-Cl) 8-16 Me Me H 6-Br Ph(2,6-F₂) 8-17 Me Me H 6-Br Ph(2,6-Cl₂)8-18 Me Me H 6-CF₃ Ph(2,6-F₂) 8-19 Me Me H 6-CN Ph(2,6-F₂) 8-20 Me CN HH Ph(2,6-F₂) 8-21 Me CO₂Et H H Ph(2,6-F₂) 8-22 Me CN H 6-Cl Ph(2,6-F₂)8-23 Me CO₂Et H 6-Cl Ph(2,6-F₂) 8-24 Me Et H H Ph(2,6-F₂) 8-25 Me MeCOMe H Ph(2,6-F₂) 8-26 Me Me CH₂OMe H Ph(2,6-F₂) 8-27 Me Me H H1-naphthyl 8-28 Me Me H H 2-naphthyl 8-29 Me Me H H 2-thienyl 8-30 Me MeH H 3-thienyl 8-31 Me Me H H 2-pyrazinyl 8-32 Me Me H H 2-pyridyl 8-33Me Me H H 3-pyridyl 8-34 Me Me H H 4-trifluoromethyl-3-pyridyl 8-35 MeMe H H 4-pyridyl 8-36 Me Me H H 2-furyl 8-37 Me Me H H 3-furyl 8-38 MeMe H 5-Cl Ph(2-F) 8-39 Me Me H 5-Cl Ph(2,6-F₂) 8-40 Me Me H 5-Br Ph(2-F)8-41 Me Me H 5-Br Ph(2,6-F₂) 8-42 Me Me H 5-CF₃ Ph(2-F) 8-43 Me Me H5-CF₃ Ph(2,6-F₂) 116-119 8-44 Me Me H 5-OSO₂CF₃ Ph(2-F) 8-45 Me Me H5-OSO₂CF₃ Ph(2,6-F₂) 8-46 Me Me H 5-OCH₂CF₃ Ph(2-F) 8-47 Me Me H5-OCH₂CF₃ Ph(2,6-F₂) 8-48 Me Me H 3-Cl Ph(2-F) 8-49 Me Me H 3-ClPh(2,6-F₂) 8-50 Me Me H 3-Cl Ph(2-Cl) 8-51 Me Me H 3-Cl Ph(2-Me) 8-52 MeMe H 3-Cl Ph(2-CF₃) 8-53 Me Me H 3-Cl Ph(2-F-6-Cl) 8-54 Me Me H 3-MePh(2-F) 8-55 Me Me H 3-Me Ph(2,6-F₂) 8-56 Me Me H 3-Me Ph(2-Cl) 8-57 MeMe H 3-Me Ph(2-Me) 8-58 Me Me H 3-Me Ph(2-CF₃) 8-59 Me Me H 3-MePh(2-F-6-Cl) 8-60 Me Me H 5-Me Ph(2-F) 8-61 Me Me H 5-Me Ph(2,6-F₂) 8-62Me Me H 5-Me Ph(2-Cl) 8-63 Me Me H 5-Me Ph(2-Me) 8-64 Me Me H 5-MePh(2-CF₃) 8-65 Me Me H 5-Me Ph(2-F-6-Cl) 8-66 Me Me H 6-Me Ph(2-F) 8-67Me Me H 6-Me Ph(2,6-F₂) 8-68 Me Me H 6-Me Ph(2-Cl) 8-69 Me Me H 6-MePh(2-Me) 8-70 Me Me H 6-Me Ph(2-CF₃) 8-71 Me Me H 6-Me Ph(2-F-6-Cl) 8-72Me Me H 5-OCF₃ Ph(2-F) 8-73 Me Me H 5-OCF₃ Ph(2,6-F₂) 8-74 Me Me H5-OCF₃ Ph(2-Cl) 8-75 Me Me H 5-OCF₃ Ph(2-Me) 8-76 Me Me H 5-OCF₃Ph(2-CF₃) 8-77 Me Me H 5-OCF₃ Ph(2-F-6-Cl) 8-78 Me Me H 6-OCF₃ Ph(2-F)8-79 Me Me H 6-OCF₃ Ph(2,6-F₂) 8-80 Me Me H 6-OCF₃ Ph(2-Cl) 8-81 Me Me H6-OCF₃ Ph(2-Me) 8-82 Me Me H 6-OCF₃ Ph(2-CF₃) 8-83 Me Me H 6-OCF₃Ph(2-F-6-Cl) 8-84 Me Me H 5-OCHF₂ Ph(2-F) 8-85 Me Me H 5-OCHF₂Ph(2,6-F₂) 8-86 Me Me H 5-OCHF₂ Ph(2-Cl) 8-87 Me Me H 5-OCHF₂ Ph(2-Me)8-88 Me Me H 5-OCHF₂ Ph(2-CF₃) 8-89 Me Me H 5-OCHF₂ Ph(2-F-6-Cl) 8-90 MeMe H 6-OCHF₂ Ph(2-F) 8-91 Me Me H 6-OCHF₂ Ph(2,6-F₂) 8-92 Me Me H6-OCHF₂ Ph(2-Cl) 8-93 Me Me H 6-OCHF₂ Ph(2-Me) 8-94 Me Me H 6-OCHF₂Ph(2-CF₃) 8-95 Me Me H 6-OCHF₂ Ph(2-F-6-Cl) 8-96 Me Me H 3,5-Cl₂ Ph(2-F)8-97 Me Me H 3,5-Cl₂ Ph(2,6-F₂) 8-98 Me Me H 3,5-Cl₂ Ph(2-Cl) 8-99 Me MeH 3,5-Cl₂ Ph(2-Me) 8-100 Me Me H 3,5-Cl₂ Ph(2-CF₃) 8-101 Me Me H 3,5-Cl₂Ph(2-F-6-Cl) 8-102 Me Me H 4,5-Cl₂ Ph(2-F) 8-103 Me Me H 4,5-Cl₂Ph(2,6-F₂) 8-104 Me Me H 4,5-Cl₂ Ph(2-Cl) 8-105 Me Me H 4,5-Cl₂ Ph(2-Me)8-106 Me Me H 4,5-Cl₂ Ph(2-CF₃) 8-107 Me Me H 4,5-Cl₂ Ph(2-F-6-Cl) 8-108Me Me H 3-Cl-5-Br Ph(2-F) 8-109 Me Me H 3-Cl-5-Br Ph(2,6-F₂) 8-110 Me MeH 3-Cl-5-Br Ph(2-Cl) 8-111 Me Me H 3-Cl-5-Br Ph(2-Me) 8-112 Me Me H3-Cl-5-Br Ph(2-CF₃) 8-113 Me Me H 3-Cl-5-Br Ph(2-F-6-Cl) 8-114 Me Me H4-Cl-5-Br Ph(2-F) 8-115 Me Me H 4-Cl-5-Br Ph(2,6-F₂) 8-116 Me Me H4-Cl-5-Br Ph(2-Cl) 8-117 Me Me H 4-Cl-5-Br Ph(2-Me) 8-118 Me Me H4-Cl-5-Br Ph(2-CF₃) 8-119 Me Me H 4-Cl-5-Br Ph(2-F-6-Cl) 8-120 Me Me H3-Cl-5-CF₃ Ph(2-F) 8-121 Me Me H 3-Cl-5-CF₃ Ph(2,6-F₂) 159-162 8-122 MeMe H 3-Cl-5-CF₃ Ph(2-Cl) 8-123 Me Me H 3-Cl-5-CF₃ Ph(2-Me) 8-124 Me Me H3-Cl-5-CF₃ Ph(2-CF₃) 8-125 Me Me H 3-Cl-5-CF₃ Ph(2-F-6-Cl) 8-126 Me Me H4-Cl-5-CF₃ Ph(2-F) 8-127 Me Me H 4-Cl-5-CF₃ Ph(2,6-F₂) 8-128 Me Me H4-Cl-5-CF₃ Ph(2-Cl) 8-129 Me Me H 4-Cl-5-CF₃ Ph(2-Me) 8-130 Me Me H4-Cl-5-CF₃ Ph(2-CF₃) 8-131 Me Me H 4-Cl-5-CF₃ Ph(2-F-6-Cl) 8-132 Me Me H3-Cl-5-OCF₃ Ph(2-F) 8-133 Me Me H 3-Cl-5-OCF₃ Ph(2,6-F₂) 8-134 Me Me H3-Cl-5-OCF₃ Ph(2-Cl) 8-135 Me Me H 3-Cl-5-OCF₃ Ph(2-Me) 8-136 Me Me H3-Cl-5-OCF₃ Ph(2-CF₃) 8-137 Me Me H 3-Cl-5-OCF₃ Ph(2-F-6-Cl) 8-138 Me MeH 4-Cl-5-OCF₃ Ph(2-F) 8-139 Me Me H 4-Cl-5-OCF₃ Ph(2,6-F₂) 8-140 Me Me H4-Cl-5-OCF₃ Ph(2-Cl) 8-141 Me Me H 4-Cl-5-OCF₃ Ph(2-Me) 8-142 Me Me H4-Cl-5-OCF₃ Ph(2-CF₃) 8-143 Me Me H 4-Cl-5-OCF₃ Ph(2-F-6-Cl) 8-144 Me MeH 3-Cl-5-OCHF₂ Ph(2-F) 8-145 Me Me H 3-Cl-5-OCHF₂ Ph(2,6-F₂) 8-146 Me MeH 3-Cl-5-OCHF₂ Ph(2-Cl) 8-147 Me Me H 3-Cl-5-OCHF₂ Ph(2-Me) 8-148 Me MeH 3-Cl-5-OCHF₂ Ph(2-CF₃) 8-149 Me Me H 3-Cl-5-OCHF₂ Ph(2-F-6-Cl) 8-150Me Me H 4-Cl-5-OCHF₂ Ph(2-F) 8-151 Me Me H 4-Cl-5-OCHF₂ Ph(2,6-F₂) 8-152Me Me H 4-Cl-5-OCHF₂ Ph(2-Cl) 8-153 Me Me H 4-Cl-5-OCHF₂ Ph(2-Me) 8-154Me Me H 4-Cl-5-OCHF₂ Ph(2-CF₃) 8-155 Me Me H 4-Cl-5-OCHF₂ Ph(2-F-6-Cl)8-156 Me Me H 3-Cl-5-OCH₂CF₃ Ph(2-F) 8-157 Me Me H 3-Cl-5-OCH₂CF₃Ph(2,6-F₂) 8-158 Me Me H 3-Cl-5-OCH₂CF₃ Ph(2-Cl) 8-159 Me Me H3-Cl-5-OCH₂CF₃ Ph(2-Me) 8-160 Me Me H 3-Cl-5-OCH₂CF₃ Ph(2-CF₃) 8-161 MeMe H 3-Cl-5-OCH₂CF₃ Ph(2-F-6-Cl) 8-162 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2-F)8-163 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2,6-F₂) 8-164 Me Me H 4-Cl-5-OCH₂CF₃Ph(2-Cl) 8-165 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2-Me) 8-166 Me Me H4-Cl-5-OCH₂CF₃ Ph(2-CF₃) 8-167 Me Me H 4-Cl-5-OCH₂CF₃ Ph(2-F-6-Cl) 8-168Me Me H 3-Me-5-Cl Ph(2-F) 8-169 Me Me H 3-Me-5-Cl Ph(2,6-F₂) 8-170 Me MeH 3-Me-5-Cl Ph(2-Cl) 8-171 Me Me H 3-Me-5-Cl Ph(2-Me) 8-172 Me Me H3-Me-5-Cl Ph(2-CF₃) 8-173 Me Me H 3-Me-5-Cl Ph(2-F-6-Cl) 8-174 Me Me H4-Me-5-Cl Ph(2-F) 8-175 Me Me H 4-Me-5-Cl Ph(2,6-F₂) 8-176 Me Me H4-Me-5-Cl Ph(2-Cl) 8-177 Me Me H 4-Me-5-Cl Ph(2-Me) 8-178 Me Me H4-Me-5-Cl Ph(2-CF₃) 8-179 Me Me H 4-Me-5-Cl Ph(2-F-6-Cl) 8-180 Me Me H3-Me-5-Br Ph(2-F) 8-181 Me Me H 3-Me-5-Br Ph(2,6-F₂) 8-182 Me Me H3-Me-5-Br Ph(2-Cl) 8-183 Me Me H 3-Me-5-Br Ph(2-Me) 8-184 Me Me H3-Me-5-Br Ph(2-CF₃) 8-185 Me Me H 3-Me-5-Br Ph(2-F-6-Cl) 8-186 Me Me H4-Me-5-Br Ph(2-F) 8-187 Me Me H 4-Me-5-Br Ph(2,6-F₂) 8-188 Me Me H4-Me-5-Br Ph(2-Cl) 8-189 Me Me H 4-Me-5-Br Ph(2-Me) 8-190 Me Me H4-Me-5-Br Ph(2-CF₃) 8-191 Me Me H 4-Me-5-Br Ph(2-F-6-Cl) 8-192 Me Me H3-Me-5-CF₃ Ph(2-F) 8-193 Me Me H 3-Me-5-CF₃ Ph(2,6-F₂) 8-194 Me Me H3-Me-5-CF₃ Ph(2-Cl) 8-195 Me Me H 3-Me-5-CF₃ Ph(2-Me) 8-196 Me Me H3-Me-5-CF₃ Ph(2-CF₃) 8-197 Me Me H 3-Me-5-CF₃ Ph(2-F-6-Cl) 8-198 Me Me H4-Me-5-CF₃ Ph(2-F) 8-199 Me Me H 4-Me-5-CF₃ Ph(2,6-F₂) 8-200 Me Me H4-Me-5-CF₃ Ph(2-Cl) 8-201 Me Me H 4-Me-5-CF₃ Ph(2-Me) 8-202 Me Me H4-Me-5-CF₃ Ph(2-CF₃) 8-203 Me Me H 4-Me-5-CF₃ Ph(2-F-6-Cl) 8-204 Me Me H3-Me-5-OCF₃ Ph(2-F) 8-205 Me Me H 3-Me-5-OCF₃ Ph(2,6-F₂) 8-206 Me Me H3-Me-5-OCF₃ Ph(2-Cl) 8-207 Me Me H 3-Me-5-OCF₃ Ph(2-Me) 8-208 Me Me H3-Me-5-OCF₃ Ph(2-CF₃) 8-209 Me Me H 3-Me-5-OCF₃ Ph(2-F-6-Cl) 8-210 Me MeH 4-Me-5-OCF₃ Ph(2-F) 8-211 Me Me H 4-Me-5-OCF₃ Ph(2,6-F₂) 8-212 Me Me H4-Me-5-OCF₃ Ph(2-Cl) 8-213 Me Me H 4-Me-5-OCF₃ Ph(2-Me) 8-214 Me Me H4-Me-5-OCF₃ Ph(2-CF₃) 8-215 Me Me H 4-Me-5-OCF₃ Ph(2-F-6-Cl) 8-216 Me MeH 3-Me-5-OCHF₂ Ph(2-F) 8-217 Me Me H 3-Me-5-OCHF₂ Ph(2,6-F₂) 8-218 Me MeH 3-Me-5-OCHF₂ Ph(2-Cl) 8-219 Me Me H 3-Me-5-OCHF₂ Ph(2-Me) 8-220 Me MeH 3-Me-5-OCHF₂ Ph(2-CF₃) 8-221 Me Me H 3-Me-5-OCHF₂ Ph(2-F-6-Cl) 8-222Me Me H 4-Me-5-OCHF₂ Ph(2-F) 8-223 Me Me H 4-Me-5-OCHF₂ Ph(2,6-F₂) 8-224Me Me H 4-Me-5-OCHF₂ Ph(2-Cl) 8-225 Me Me H 4-Me-5-OCHF₂ Ph(2-Me) 8-226Me Me H 4-Me-5-OCHF₂ Ph(2-CF₃) 8-227 Me Me H 4-Me-5-OCHF₂ Ph(2-F-6-Cl)8-228 Me Me H 3-Me-5-OCH₂CF₃ Ph(2-F) 8-229 Me Me H 3-Me-5-OCH₂CF₃Ph(2,6-F₂) 8-230 Me Me H 3-Me-5-OCH₂CF₃ Ph(2-Cl) 8-231 Me Me H3-Me-5-OCH₂CF₃ Ph(2-Me) 8-232 Me Me H 3-Me-5-OCH₂CF₃ Ph(2-CF₃) 8-233 MeMe H 3-Me-5-OCH₂CF₃ Ph(2-F-6-Cl) 8-234 Me Me H 4-Me-5-OCH₂CF₃ Ph(2-F)8-235 Me Me H 4-Me-5-OCH₂CF₃ Ph(2,6-F₂) 8-236 Me Me H 4-Me-5-OCH₂CF₃Ph(2-Cl) 8-237 Me Me H 4-Me-5-OCH₂CF₃ Ph(2-Me) 8-238 Me Me H4-Me-5-OCH₂CF₃ Ph(2-CF₃) 8-239 Me Me H 4-Me-5-OCH₂CF₃ Ph(2-F-6-Cl)

TABLE 9

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 9-1 Me Me H H Ph9-2 Me Me H H Ph(2-F) 9-3 Me Me H H Ph(2-Cl) 9-4 Me Me H H Ph(2-OMe) 9-5Me Me H H Ph(2,6-F₂) 223-226 9-6 Me Me H H Ph(2,6-Cl₂) 9-7 Me Me H HPh(2,6-OMe₂) 9-8 Me Me H 6-Cl Ph 9-9 Me Me H 6-Cl Ph(2-F) 9-10 Me Me H6-Cl Ph(2-Cl) 9-11 Me Me H 6-Cl Ph(2,.6-F₂) 9-12 Me Me H 6-ClPh(2,6-Cl₂) 9-13 Me Me H 6-Br Ph 9-14 Me Me H 6-Br Ph(2-F) 9-15 Me Me H6-Br Ph(2-Cl) 9-16 Me Me H 6-Br Ph(2,6-F₂) 9-17 Me Me H 6-Br Ph(2,6-Cl₂)9-18 Me Me H 6-CF₃ Ph(2,6-F₂) 9-19 Me Me H 6-CN Ph(2,6-F₂) 9-20 Me CN HH Ph(2,6-F₂) 9-21 Me CO₂Et H H Ph(2,6-F₂) 9-22 Me CN H 6-Cl Ph(2,6-F₂)9-23 Me CO₂Et H 6-Cl Ph(2,6-F₂) 9-24 Me Et H H Ph(2,6-F₂) 9-25 Me MeCOMe H Ph(2,6-F₂) 9-26 Me Me CH₂OMe H Ph(2,6-F₂) 9-27 Me Me H H1-naphthyl 9-28 Me Me H H 2-naphthyl 9-29 Me Me H H 2-thienyl 9-30 Me MeH H 3-thienyl 9-31 Me Me H H 2-pyrazinyl 9-32 Me Me H H 2-pyridyl 9-33Me Me H H 3-pyridyl 9-34 Me Me H H 4- trifluoromethyl- 3-pyridyl 9-35 MeMe H H 4-pyridyl 9-36 Me Me H H 2-furyl 9-37 Me Me H H 3-furyl 9-38 MeMe H 6-OSO₂CF₃ Ph(2-F) 9-39 Me Me H 6-OSO₂CF₃ Ph(2,6-F₂) 9-40 Me Me H6-OCH₂CF₃ Ph(2-F) 9-41 Me Me H 6-OCH₂CF₃ Ph(2,6-F₂) 9-42 Me Me H 2-ClPh(2-F) 9-43 Me Me H 2-Cl Ph(2,6-F₂) 9-44 Me Me H 2-Cl Ph(2-Cl) 9-45 MeMe H 2-Cl Ph(2-Me) 9-46 Me Me H 2-Cl Ph(2-CF₃) 9-47 Me Me H 2-ClPh(2-F-6-Cl) 9-48 Me Me H 4-Cl Ph(2-F) 9-49 Me Me H 4-Cl Ph(2,6-F₂) 9-50Me Me H 4-Cl Ph(2-Cl) 9-51 Me Me H 4-Cl Ph(2-Me) 9-52 Me Me H 4-ClPh(2-CF₃) 9-53 Me Me H 4-Cl Ph(2-F-6-Cl) 9-54 Me Me H 5-Cl Ph(2-F) 9-55Me Me H 5-Cl Ph(2,6-F₂) 9-56 Me Me H 5-Cl Ph(2-Cl) 9-57 Me Me H 5-ClPh(2-Me) 9-58 Me Me H 5-Cl Ph(2-CF₃) 9-59 Me Me H 5-Cl Ph(2-F-6-Cl) 9-60Me Me H 5-Br Ph(2-F) 9-61 Me Me H 5-Br Ph(2,6-F₂) 9-62 Me Me H 5-BrPh(2-Cl) 9-63 Me Me H 5-Br Ph(2-Me) 9-64 Me Me H 5-Br Ph(2-CF₃) 9-65 MeMe H 5-Br Ph(2-F-6-Cl) 9-66 Me Me H 2-Me Ph(2-F) 9-67 Me Me H 2-MePh(2,6-F₂) 9-68 Me Me H 2-Me Ph(2-Cl) 9-69 Me Me H 2-Me Ph(2-Me) 9-70 MeMe H 2-Me Ph(2-CF₃) 9-71 Me Me H 2-Me Ph(2-F-6-Cl) 9-72 Me Me H 4-MePh(2-F) 9-73 Me Me H 4-Me Ph(2,6-F₂) 9-74 Me Me H 4-Me Ph(2-Cl) 9-75 MeMe H 4-Me Ph(2-Me) 9-76 Me Me H 4-Me Ph(2-CF₃) 9-77 Me Me H 4-MePh(2-F-6-Cl) 9-78 Me Me H 5-Me Ph(2-F) 9-79 Me Me H 5-Me Ph(2,6-F₂) 9-80Me Me H 5-Me Ph(2-Cl) 9-81 Me Me H 5-Me Ph(2-Me) 9-82 Me Me H 5-MePh(2-CF₃) 9-83 Me Me H 5-Me Ph(2-F-6-Cl) 9-84 Me Me H 6-Me Ph(2-F) 9-85Me Me H 6-Me Ph(2,6-F₂) 9-86 Me Me H 6-Me Ph(2-Cl) 9-87 Me Me H 6-MePh(2-Me) 9-88 Me Me H 6-Me Ph(2-CF₃) 9-89 Me Me H 6-Me Ph(2-F-6-Cl) 9-90Me Me H 5-CN Ph(2-F) 9-91 Me Me H 5-CN Ph(2,6-F₂) 9-92 Me Me H 5-CNPh(2-Cl) 9-93 Me Me H 5-CN Ph(2-Me) 9-94 Me Me H 5-CN Ph(2-CF₃) 9-95 MeMe H 5-CN Ph(2-F-6-Cl) 9-96 Me Me H 5-CF₃ Ph(2-F) 9-97 Me Me H 5-CF₃Ph(2,6-F₂) 9-98 Me Me H 5-CF₃ Ph(2-Cl) 9-99 Me Me H 5-CF₃ Ph(2-Me) 9-100Me Me H 5-CF₃ Ph(2-CF₃) 9-101 Me Me H 5-CF₃ Ph(2-F-6-Cl) 9-102 Me Me H5-OCF₃ Ph(2-F) 9-103 Me Me H 5-OCF3 Ph(2,6-F₂) 9-104 Me Me H 5-OCF3Ph(2-Cl) 9-105 Me Me H 5-OCF3 Ph(2-Me) 9-106 Me Me H 5-OCF3 Ph(2-CF₃)9-107 Me Me H 5-OCF3 Ph(2-F-6-Cl) 9-108 Me Me H 6-OCF3 Ph(2-F) 9-109 MeMe H 6-OCF3 Ph(2,6-F₂) 9-110 Me Me H 6-OCF3 Ph(2-Cl) 9-111 Me Me H6-OCF3 Ph(2-Me) 9-112 Me Me H 6-OCF3 Ph(2-CF₃) 9-113 Me Me H 6-OCF3Ph(2-F-6-Cl) 9-114 Me Me H 5-OCHF2 Ph(2-F) 9-115 Me Me H 5-OCHF2Ph(2,6-F₂) 9-116 Me Me H 5-OCHF2 Ph(2-Cl) 9-117 Me Me H 5-OCHF2 Ph(2-Me)9-118 Me Me H 5-OCHF2 Ph(2-CF₃) 9-119 Me Me H 5-OCHF2 Ph(2-F-6-Cl) 9-120Me Me H 6-OCHF2 Ph(2-F) 9-121 Me Me H 6-OCHF2 Ph(2,6-F₂) 9-122 Me Me H6-OCHF2 Ph(2-Cl) 9-123 Me Me H 6-OCHF2 Ph(2-Me) 9-124 Me Me H 6-OCHF2Ph(2-CF₃) 9-125 Me Me H 6-OCHF2 Ph(2-F-6-Cl) 9-126 Me Me H 2,6-Cl₂Ph(2-F) 9-127 Me Me H 2,6-Cl₂ Ph(2,6-F₂) 9-128 Me Me H 2,6-Cl₂ Ph(2-Cl)9-129 Me Me H 2,6-Cl₂ Ph(2-Me) 9-130 Me Me H 2,6-Cl₂ Ph(2-CF₃) 9-131 MeMe H 2,6-Cl₂ Ph(2-F-6-Cl) 9-132 Me Me H 4,6-Cl₂ Ph(2-F) 9-133 Me Me H4,6-Cl₂ Ph(2,6-F₂) 9-134 Me Me H 4,6-Cl₂ Ph(2-Cl) 9-135 Me Me H 4,6-Cl₂Ph(2-Me) 9-136 Me Me H 4,6-Cl₂ Ph(2-CF₃) 9-137 Me Me H 4,6-Cl₂Ph(2-F-6-Cl) 9-138 Me Me H 5,6-Cl₂ Ph(2-F) 9-139 Me Me H 5,6-Cl₂Ph(2,6-F₂) 9-140 Me Me H 5,6-Cl₂ Ph(2-Cl) 9-141 Me Me H 5,6-Cl₂ Ph(2-Me)9-142 Me Me H 5,6-Cl₂ Ph(2-CF₂) 9-143 Me Me H 5,6-Cl₂ Ph(2-F-6-Cl) 9-144Me Me H 2-Cl-6-Br Ph(2-F) 9-145 Me Me H 2-C1-6-Br Ph(2,6-F₂) 9-146 Me MeH 2-Cl-6-Br Ph(2-Cl) 9-147 Me Me H 2-Cl-6-Br Ph(2-Me) 9-148 Me Me H2-Cl-6-Br Ph(2-CF₃) 9-149 Me Me H 2-Cl-6-Br Ph(2-F-6-Cl) 9-150 Me Me H4-C1-6-Br Ph(2-F) 9-151 Me Me H 4-Cl-6-Br ph(2,6-F₂) 9-152 Me Me H4-Cl-6-Br Ph(2-Cl) 9-153 Me Me H 4-Cl-6-Br Ph(2-Me) 9-154 Me Me H4-Cl-6-Br Ph(2-CF₃) 9-155 Me Me H 4-Cl-6-Br Ph(2-F-6-Cl) 9-156 Me Me H5-Cl-6-Br Ph(2-F) 9-157 Me Me H 5-Cl-6-Br Ph(2,6-F₂) 9-158 Me Me H5-Cl-6-Br Ph(2-Cl) 9-159 Me Me H 5-Cl-6-Br Ph(2-Me) 9-160 Me Me H5-Cl-6-Br Ph(2-CF₃) 9-161 Me Me H 5-Cl-6-Br Ph(2-F-6-Cl) 9-162 Me Me H2-Cl-6-CF₃ Ph(2-F) 9-163 Me Me H 2-Cl-6-CF₃ Ph(2,6-F₂) 9-164 Me Me H2-Cl-6-CF₃ Ph(2-Cl) 9-165 Me Me H 2-Cl-6-CF₃ Ph(2-Me) 9-166 Me Me H2-Cl-6-CF₃ Ph(2-CF₃) 9-167 Me Me H 2-Cl-6-CF₃ Ph(2-F-6-Cl) 9-168 Me Me H4-Cl-6-CF₃ Ph(2-F) 9-169 Me Me H 4-Cl-6-CF₃ Ph(2,6-F₂) 9-170 Me Me H4-Cl-6-CF₃ Ph(2-Cl) 9-171 Me Me H 4-Cl-6-CF₃ Ph(2-Me) 9-172 Me Me H4-Cl-6-CF₃ Ph(2-CF₃) 9-173 Me Me H 4-Cl-6-CF₃ Ph(2-F-6-Cl) 9-174 Me Me H5-Cl-6-CF₃ Ph(2-F) 9-175 Me Me H 5-Cl-6-CF₃ Ph(2,6-F₂) 9-176 Me Me H5-Cl-6-CF₃ Ph(2-Cl) 9-177 Me Me H 5-Cl-6-CF₃ Ph(2-Me) 9-178 Me Me H5-Cl-6-CF₃ Ph(2-CF₃) 9-179 Me Me H 5-Cl-6-CF₃ Ph(2-F-6-Cl) 9-180 Me Me H2-Cl-6-OCF₃ Ph(2-F) 9-181 Me Me H 2-Cl-6-OCF₃ Ph(2,6-F₂) 9-182 Me Me H2-Cl-6-OCF₃ Ph(2-Cl) 9-183 Me Me H 2-Cl-6-OCF₃ Ph(2-Me) 9-184 Me Me H2-Cl-6-OCF₃ Ph(2-CF₃) 9-185 Me Me H 2-Cl-6-OCF₃ Ph(2-F-6-Cl) 9-186 Me MeH 4-Cl-6-OCF₃ Ph(2-F) 9-187 Me Me H 4-Cl-6-OCF₃ Ph(2,6-F₂) 9-188 Me Me H4-Cl-6-OCF₃ Ph(2-Cl) 9-189 Me Me H 4-Cl-6-OCF₃ Ph(2-Me) 9-190 Me Me H4-Cl-6-OCF₃ Ph(2-CF₃) 9-191 Me Me H 4-Cl-6-OCF₃ Ph(2-F-6-Cl) 9-192 Me MeH 5-Cl-6-OCF₃ Ph(2-F) 9-193 Me Me H 5-Cl-6-OCF₃ Ph(2,6-F₂) 9-194 Me Me H5-Cl-6-OCF₃ Ph(2-Cl) 9-195 Me Me H 5-Cl-6-OCF₃ Ph(2-Me) 9-196 Me Me H5-Cl-6-OCF₃ Ph(2-CF₃) 9-197 Me Me H 5-Cl-6-OCF₃ Ph(2-F-6-Cl) 9-198 Me MeH 2-Cl-6-OCHF₂ Ph(2-F) 9-199 Me Me H 2-Cl-6-OCHF₂ Ph(2,6-F₂) 9-200 Me MeH 2-Cl-6-OCHF₂ Ph(2-Cl) 9-201 Me Me H 2-Cl-6-OCHF₂ Ph(2-Me) 9-202 Me MeH 2-Cl-6-OCHF₂ Ph(2-CF₃) 9-203 Me Me H 2-Cl-6-OCHF₂ Ph(2-F-6-Cl) 9-204Me Me H 4-Cl-6-OCHF₂ Ph(2-F) 9-205 Me Me H 4-Cl-6-OCHF₂ Ph(2,6-F₂) 9-206Me Me H 4-Cl-6-OCHF₂ Ph(2-Cl) 9-207 Me Me H 4-Cl-6-OCHF₂ Ph(2-Me) 9-208Me Me H 4-Cl-6-OCHF₂ Ph(2-CF₃) 9-209 Me Me H 4-Cl-6-OCHF₂ Ph(2-F-6-Cl)9-210 Me Me H 5-Cl-6-OCHF₂ Ph(2-F) 9-211 Me Me H 5-Cl-6-OCHF₂ Ph(2,6-F₂)9-212 Me Me H 5-Cl-6-OCHF₂ Ph(2-Cl) 9-213 Me Me H 5-Cl-6-OCHF₂ Ph(2-Me)9-214 Me Me H 5-Cl-6-OCHF₂ Ph(2-CF₃) 9-215 Me Me H 5-Cl-6-OCHF₂Ph(2-F-6-Cl) 9-216 Me Me H 2-Cl-6-OCH₂CF₃ Ph(2-F) 9-217 Me Me H2-Cl-6-OCH₂CF₃ Ph(2,6-F₂) 9-218 Me Me H 2-Cl-6-OCH₂CF₃ Ph(2-Cl) 9-219 MeMe H 2-Cl-6-OCH₂CF₃ Ph(2-Me) 9-220 Me Me H 2-Cl-6-OCH₂CF₃ Ph(2-CF₃)9-221 Me Me H 2-Cl-6-OCH₂CF₃ Ph(2-F-6-Cl) 9-222 Me Me H 4-Cl-6-OCH₂CF₃Ph(2-F) 9-223 Me Me H 4-Cl-6-OCH₂CF₃ Ph(2,6-F₂) 9-224 Me Me H4-Cl-6-OCH₂CF₃ Ph(2-Cl) 9-225 Me Me H 4-Cl-6-OCH₂CF₃ Ph(2-Me) 9-226 MeMe H 4-Cl-6-OCH₂CF₃ Ph(2-CF₃) 9-227 Me Me H 4-Cl-6-OCH₂CF₃ Ph(2-F-6-Cl)9-228 Me Me H 5-Cl-6-OCH₂CF₃ Ph(2-F) 9-229 Me Me H 5-Cl-6-OCH₂CF₃Ph(2,6-F₂) 9-230 Me Me H 5-Cl-6-OCH₂CF₃ Ph(2-Cl) 9-231 Me Me H5-Cl-6-OCH₂CF₃ Ph(2-Me) 9-232 Me Me H 5-Cl-6-OCH₂CF₃ Ph(2-CF₃) 9-233 MeMe H 5-Cl-6-OCH₂CF₃ Ph(2-F-6-Cl) 9-234 Me Me H 2-Me-6-Cl Ph(2-F) 9-235Me Me H 2-Me-6-Cl Ph(2,6-F₂) 9-236 Me Me H 2-Me-6-Cl Ph(2-Cl) 9-237 MeMe H 2-Me-6-Cl Ph(2-Me) 9-238 Me Me H 2-Me-6-Cl Ph(2-CF₃) 9-239 Me Me H2-Me-6-Cl Ph(2-F-6-Cl) 9-240 Me Me H 4-Me-6-Cl Ph(2-F) 9-241 Me Me H4-Me-6-Cl Ph(2,6-F₂) 9-242 Me Me H 4-Me-6-Cl Ph(2-Cl) 9-243 Me Me H4-Me-6-Cl Ph(2-Me) 9-244 Me Me H 4-Me-6-Cl Ph(2-CF₃) 9-245 Me Me H4-Me-6-Cl Ph(2-F-6-Cl) 9-246 Me Me H 5-Me-6-Cl Ph(2-F) 9-247 Me Me H5-Me-6-Cl Ph(2,6-F₂) 9-248 Me Me H 5-Me-6-Cl Ph(2-Cl) 9-249 Me Me H5-Me-6-Cl Ph(2-Me) 9-250 Me Me H 5-Me-6-Cl Ph(2-CF₃) 9-251 Me Me H5-Me-6-Cl Ph(2-F-6-Cl) 9-252 Me Me H 2-Me-6-Br Ph(2-F) 9-253 Me Me H2-Me-6-Br Ph(2,6-F₂) 9-254 Me Me H 2-Me-6-Br Ph(2-Cl) 9-255 Me Me H2-Me-6-Br Ph(2-Me) 9-256 Me Me H 2-Me-6-Br Ph(2-CF₃) 9-257 Me Me H2-Me-6-Br Ph(2-F-6-Cl) 9-258 Me Me H 4-Me-6-Br Ph(2-F) 9-259 Me Me H4-Me-6-Br Ph(2,6-F₂) 9-260 Me Me H 4-Me-6-Br Ph(2-Cl) 9-261 Me Me H4-Me-6-Br Ph(2-Me) 9-262 Me Me H 4-Me-6-Br Ph(2-CF₃) 9-263 Me Me H4-Me-6-Br Ph(2-F-6-Cl) 9-264 Me Me H 5-Me-6-Br Ph(2-F) 9-265 Me Me H5-Me-6-Br Ph(2,6-F₂) 9-266 Me Me H 5-Me-6-Br Ph(2-Cl) 9-267 Me Me H5-Me-6-Br Ph(2-Me) 9-268 Me Me H 5-Me-6-Br Ph(2-CF₃) 9-269 Me Me H5-Me-6-Br Ph(2-F-6-Cl) 9-270 Me Me H 2-Me-6-CF₃ Ph(2-F) 9-271 Me Me H2-Me-6-CF₃ Ph(2,6-F₂) 9-272 Me Me H 2-Me-6-CF₃ Ph(2-Cl) 9-273 Me Me H2-Me-6-CF₃ Ph(2-Me) 9-274 Me Me H 2-Me-6-CF₃ Ph(2-CF₃) 9-275 Me Me H2-Me-6-CF₃ Ph(2-F-6-Cl) 9-276 Me Me H 4-Me-6-CF₃ Ph(2-F) 9-277 Me Me H4-Me-6-CF₃ Ph(2,6-F₂) 9-278 Me Me H 4-Me-6-CF₃ Ph(2-Cl) 9-279 Me Me H4-Me-6-CF₃ Ph(2-Me) 9-280 Me Me H 4-Me-6-CF₃ Ph(2-CF₃) 9-281 Me Me H4-Me-6-CF₃ Ph(2-F-6-Cl) 9-282 Me Me H 5-Me-6-CF₃ Ph(2-F) 9-283 Me Me H5-Me-6-CF₃ Ph(2,6-F₂) 9-284 Me Me H 5-Me-6-CF₃ Ph(2-Cl) 9-285 Me Me H5-Me-6-CF₃ Ph(2-Me) 9-286 Me Me H 5-Me-6-CF₃ Ph(2-CF₃) 9-287 Me Me H5-Me-6-CF₃ Ph(2-F-6-Cl) 9-288 Me Me H 2-Me-6-OCF₃ Ph(2-F) 9-289 Me Me H2-Me-6-OCF₃ Ph(2,6-F₂) 9-290 Me Me H 2-Me-6-OCF₃ Ph(2-Cl) 9-291 Me Me H2-Me-6-OCF₃ Ph(2-Me) 9-292 Me Me H 2-Me-6-OCF₃ Ph(2-CF₃) 9-293 Me Me H2-Me-6-OCF₃ Ph(2-F-6-Cl) 9-294 Me Me H 4-Me-6-OCF₃ Ph(2-F) 9-295 Me Me H4-Me-6-OCF₃ Ph(2,6-F₂) 9-296 Me Me H 4-Me-6-OCF₃ Ph(2-Cl) 9-297 Me Me H4-Me-6-OCF₃ Ph(2-Me) 9-298 Me Me H 4-Me-6-OCF₃ Ph(2-CF₃) 9-299 Me Me H4-Me-6-OCF₃ Ph(2-F-6-Cl) 9-300 Me Me H 5-Me-6-OCF₃ Ph(2-F) 9-301 Me Me H5-Me-6-OCF₃ Ph(2,6-F₂) 9-302 Me Me H 5-Me-6-OCF₃ Ph(2-Cl) 9-303 Me Me H5-Me-6-OCF₃ Ph(2-Me) 9-304 Me Me H 5-Me-6-OCF₃ Ph(2-CF₃) 9-305 Me Me H5-Me-6-OCF₃ Ph(2-F-6-Cl) 9-306 Me Me H 2-Me-6-OCHF₂ Ph(2-F) 9-307 Me MeH 2-Me-6-OCHF₂ Ph(2,6-F₂) 9-308 Me Me H 2-Me-6-OCHF₂ Ph(2-Cl) 9-309 MeMe H 2-Me-6-OCHF₂ Ph(2-Me) 9-310 Me Me H 2-Me-6-OCHF₂ Ph(2-CF₃) 9-311 MeMe H 2-Me-6-OCHF₂ Ph(2-F-6-Cl) 9-312 Me Me H 4-Me-6-OCHF₂ Ph(2-F) 9-313Me Me H 4-Me-6-OCHF₂ Ph(2,6-F₂) 9-314 Me Me H 4-Me-6-OCHF₂ Ph(2-Cl)9-315 Me Me H 4-Me-6-OCHF₂ Ph(2-Me) 9-316 Me Me H 4-Me-6-OCHF₂ Ph(2-CF₃)9-317 Me Me H 4-Me-6-OCHF₂ Ph(2-F-6-Cl) 9-318 Me Me H 5-Me-6-OCHF₂Ph(2-F) 9-319 Me Me H 5-Me-6-OCHF₂ Ph(2,6-F₂) 9-320 Me Me H 5-Me-6-OCHF₂Ph(2-Cl) 9-321 Me Me H 5-Me-6-OCHF₂ Ph(2-Me) 9-322 Me Me H 5-Me-6-OCHF₂Ph(2-CF₃) 9-323 Me Me H 5-Me-6-OCHF₂ Ph(2-F-6-Cl) 9-324 Me Me H2-Me-6-OCH₂CF₃ Ph(2-F) 9-325 Me Me H 2-Me-6-OCH₂CF₃ Ph(2,6-F₂) 9-326 MeMe H 2-Me-6-OCH₂CF₃ Ph(2-Cl) 9-327 Me Me H 2-Me-6-OCH₂CF₃ Ph(2-Me) 9-328Me Me H 2-Me-6-OCH₂CF₃ Ph(2-CF₃) 9-329 Me Me H 2-Me-6-OCH₂CF₃Ph(2-F-6-Cl) 9-330 Me Me H 4-Me-6-OCH₂CF₃ Ph(2-F) 9-331 Me Me H4-Me-6-OCH₂CF₃ Ph(2,6-F₂) 9-332 Me Me H 4-Me-6-OCH₂CF₃ Ph(2-Cl) 9-333 MeMe H 4-Me-6-OCH₂CF₃ Ph(2-Me) 9-334 Me Me H 4-Me-6-OCH₂CF₃ Ph(2-CF₃)9-335 Me Me H 4-Me-6-OCH₂CF₂ Ph(2-F-6-Cl) 9-336 Me Me H 5-Me-6-OCH₂CF₃Ph(2-F) 9-337 Me Me H 5-Me-6-OCH₂CF₃ Ph(2,6-F₂) 9-338 Me Me H5-Me-6-OCH₂CF₃ Ph(2-Cl) 9-339 Me Me H 5-Me-6-OCH₂CF₃ Ph(2-Me) 9-340 MeMe H 5-Me-6-OCH₂CF₃ Ph(2-CF₃) 9-341 Me Me H 5-Me-6-OCH₂CF₃ Ph(2-F-6-Cl)

TABLE 10

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 10-1 Me Me H HPh 10-2 Me Me H H Ph(2-F) 10-3 Me Me H H Ph(2-Cl) 10-4 Me Me H HPh(2-OMe) 10-5 Me Me H H Ph(2,6-F₂) 155-157 10-6 Me Me H H Ph(2,6-Cl₂)10-7 Me Me H H Ph(2,6-OMe₂) 10-8 Me Me H 2-Cl Ph 10-9 Me Me H 2-ClPh(2-F) 10-10 Me Me H 2-Cl Ph(2-Cl) 10-11 Me Me H 2-Cl Ph(2,6-F₂) 10-12Me Me H 2-Cl Ph(2,6-Cl₂) 10-13 Me Me H 2-Br Ph 19-14 Me Me H 2-BrPh(2-F) 10-15 Me Me H 2-Br Ph(2-Cl) 10-16 Me Me H 2-Br Ph(2,6-F₂) 10-17Me Me H 2-Br Ph(2,6-Cl₂) 10-18 Me Me H 2-CF₃ Ph(2,6-F₂) 10-19 Me Me H2-CN Ph(2,6-F₂) 10-20 Me CN H H Ph(2,6-F₂) 10-21 Me CO₂Et H H Ph(2,6-F₂)10-22 Me CN H 2-Cl Ph(2,6-F₂) 10-23 Me CO₂Et H 2-Cl Ph(2,6-F₂) 10-24 MeEt H H Ph(2,6-F₂) 10-25 Me Me COMe H Ph(2,6-F₂) 10-26 Me Me CH₂OMe HPh(2,6-F₂) 10-27 Me Me H H 1-naphthyl 10-28 Me Me H H 2-naphthyl 10-29Me Me H H 2-thienyl 10-30 Me Me H H 3-thienyl 10-31 Me Me H H2-pyrazinyl 10-32 Me Me H H 2-pyridyl 10-33 Me Me H H 3-pyridyl 10-34 MeMe H H 4- trifluoromethyl- 3-pyridyl 10-35 Me Me H H 4-pyridyl 10-36 MeMe H H 2-furyl 10-37 Me Me H H 3-furyl 10-38 Me Me H 3-Cl Ph(2-F) 10-39Me Me H 3-Cl Ph(2,6-F₂) 10-40 Me Me H 3-Cl Ph(2-Cl) 10-41 Me Me H 3-ClPh(2-Me) 10-42 Me Me H 3-Cl Ph(2-CF₃) 10-43 Me Me H 3-Cl Ph(2-F-6-Cl)10-44 Me Me H 3-Br Ph(2-F) 10-45 Me Me H 3-Br Ph(2,6-F₂) 10-46 Me Me H3-Br Ph(2-Cl) 10-47 Me Me H 3-Br Ph(2-Me) 10-48 Me Me H 3-Br Ph(2-CF₃)10-49 Me Me H 3-Br Ph(2-F-6-Cl) 10-50 Me Me H 2-Me Ph(2-F) 10-51 Me Me H2-Me Ph(2,6-F₂) 10-52 Me Me H 2-Me Ph(2-Cl) 10-53 Me Me H 2-Me Ph(2-Me)10-54 Me Me H 2-Me Ph(2-CF₃) 10-55 Me Me H 2-Me Ph(2-F-6-Cl) 10-56 Me MeH 3-Me Ph(2-F) 10-57 Me Me H 3-Me Ph(2,6-F₂) 10-58 Me Me H 3-Me Ph(2-Cl)10-59 Me Me H 3-Me Ph(2-Me) 10-60 Me Me H 3-Me Ph(2-CF₃) 10-61 Me Me H3-Me Ph(2-F-6-Cl) 10-62 Me Me H 3-CN Ph(2-F) 10-63 Me Me H 3-CNPh(2,6-F₂) 10-64 Me Me H 3-CN Ph(2-Cl) 10-65 Me Me H 3-CN Ph(2-Me) 10-66Me Me H 3-CN Ph(2-CF₃) 10-67 Me Me H 3-CN Ph(2-F-6-Cl) 10-68 Me Me H3-CF₃ Ph(2-F) 10-69 Me Me H 3-CF₃ Ph(2,6-F₂) 10-70 Me Me H 3-CF₃Ph(2-Cl) 10-71 Me Me H 3-CF₃ Ph(2-Me) 10-72 Me Me H 3-CF₃ Ph(2-CF₃)10-73 Me Me H 3-CF₃ Ph(2-F-6-Cl) 10-74 Me Me H 2-OCF₃ Ph(2-F) 10-75 MeMe H 2-OCF₃ Ph(2,6-F₂) 10-76 Me Me H 2-OCF₃ Ph(2-Cl) 10-77 Me Me H2-OCF₃ Ph(2-Me) 10-78 Me Me H 2-OCF₃ Ph(2-CF₃) 10-79 Me Me H 2-OCF₃Ph(2-F-6-Cl) 10-80 Me Me H 3-OCF₃ Ph(2-F) 10-81 Me Me H 3-OCF₃Ph(2,6-F₂) 10-82 Me Me H 3-OCF₃ Ph(2-Cl) 10-83 Me Me H 3-OCF₃ Ph(2-Me)10-84 Me Me H 3-OCF₃ Ph(2-CF₃) 10-85 Me Me H 3-OCF₃ Ph(2-F-6-Cl) 10-86Me Me H 2-OCHF₂ Ph(2-F) 10-87 Me Me H 2-OCHF₂ Ph(2,6-F₂) 10-88 Me Me H2-OCHF₂ Ph(2-Cl) 10-89 Me Me H 2-OCHF₂ Ph(2-Me) 10-90 Me Me H 2-OCHF₂Ph(2-CF₃) 10-91 Me Me H 2-OCHF₂ Ph(2-F-6-Cl) 10-92 Me Me H 3-OCHF₂Ph(2-F) 10-93 Me Me H 3-OCHF₂ Ph(2,6-F₂) 10-94 Me Me H 3-OCHF₂ Ph(2-Cl)10-95 Me Me H 3-OCHF₂ Ph(2-Me) 10-96 Me Me H 3-OCHF₂ Ph(2-CF₃) 10-97 MeMe H 3-OCHF₂ Ph(2-F-6-Cl) 10-98 Me Me H 2-CF₃-3-Cl Ph(2-F) 10-99 Me Me H2-CF₃-3-Cl Ph(2,6-F₂) 10-100 Me Me H 2-CF₃-3-Cl Ph(2-Cl) 10-101 Me Me H2-CF₃-3-Cl Ph(2-Me) 10-102 Me Me H 2-CF₃-3-Cl Ph(2-CF₃) 10-103 Me Me H2-CF₃-3-Cl Ph(2-F-6-Cl) 10-104 Me Me H 2-CF₃-3-Me Ph(2-F) 10-105 Me Me H2-CF₃-3-Me Ph(2,6-F₂) 10-106 Me Me H 2-CF₃-3-Me Ph(2-Cl) 10-107 Me Me H2-CF₃-3-Me Ph(2-Me) 10-108 Me Me H 2-CF₃-3-Me Ph(2-CF₃) 10-109 Me Me H2-CF₃-3-Me Ph(2-F-6-Cl) 10-110 Me Me H 2-OMe-3-Cl Ph(2-F) 10-111 Me Me H2-OMe-3-Cl Ph(2,6-F₂) 10-112 Me Me H 2-OMe-3-Cl Ph(2-Cl) 10-113 Me Me H2-OMe-3-Cl Ph(2-Me) 10-114 Me Me H 2-OMe-3-Cl Ph(2-CF₃) 10-115 Me Me H2-OMe-3-Cl Ph(2-F-6-Cl) 10-116 Me Me H 2-OMe-3-Me Ph(2-F) 10-117 Me Me H2-OMe-3-Me Ph(2,6-F₂) 10-118 Me Me H 2-OMe-3-Me Ph(2-Cl) 10-119 Me Me H2-OMe-3-Me Ph(2-Me) 10-120 Me Me H 2-OMe-3-Me Ph(2-CF₃) 10-121 Me Me H2-OMe-3-Me Ph(2-F-6-Cl) 10-122 Me Me H 2-OCF₃-3-Cl Ph(2-F) 10-123 Me MeH 2-OCF₃-3-Cl Ph(2,6-F₂) 10-124 Me Me H 2-OCF₃-3-Cl Ph(2-Cl) 10-125 MeMe H 2-OCF₃-3-Cl Ph(2-Me) 10-126 Me Me H 2-OCF₃-3-Cl Ph(2-CF₃) 10-127 MeMe H 2-OCF₃-3-Cl Ph(2-F-6-Cl) 10-128 Me Me H 2-OCF₃-3-Me Ph(2-F) 10-129Me Me H 2-OCF₃-3-Me Ph(2,6-F₂) 10-130 Me Me H 2-OCF₃-3-Me Ph(2-Cl)10-131 Me Me H 2-OCF₃-3-Me Ph(2-Me) 10-132 Me Me H 2-OCF₃-3-Me Ph(2-CF₃)10-133 Me Me H 2-OCF₃-3-Me Ph(2-F-6-Cl) 10-134 Me Me H 2-OCHF₂-3-ClPh(2-F) 10-135 Me Me H 2-OCHF₂-3-Cl Ph(2,6-F₂) 10-136 Me Me H2-OCHF₂-3-Cl Ph(2-Cl) 10-137 Me Me H 2-OCHF₂-3-Cl Ph(2-Me) 10-138 Me MeH 2-OCHF₂-3-Cl Ph(2-CF₃) 10-139 Me Me H 2-OCHF₂-3-Cl Ph(2-F-6-Cl) 10-140Me Me H 2-OCHF₂-3-Me Ph(2-F) 10-141 Me Me H 2-OCHF₂-3-Me Ph(2,6-F₂)10-142 Me Me H 2-OCHF₂-3-Me Ph(2-Cl) 10-143 Me Me H 2-OCHF₂-3-MePh(2-Me) 10-144 Me Me H 2-OCHF₂-3-Me Ph(2-CF₃) 10-145 Me Me H2-OCHF₂-3-Me Ph(2-F-6-Cl)

TABLE 11

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 11-1 Me Me H HPh 11-2 Me Me H H Ph(2-F) 94-96 11-3 Me Me H H Ph(2-Cl) 11-4 Me Me H HPh(2-OMe) 11-5 Me Me H H Ph(2,6-F2) 119-121 11-6 Me Me H H Ph(2,6-Cl₂)11-7 Me Me H H Ph(2,6-OMe₂) 11-8 Me Me H 6-Cl Ph 11-9 Me Me H 6-ClPh(2-F) 11-10 Me Me H 6-Cl ph(2-Cl) 11-11 Me Me H 6-Cl Ph(2,6-F₂) 11-12Me Me H 6-Cl ph(2,6-Cl₂) 11-13 Me Me H 6-Br Ph 11-14 Me Me H 6-BrPh(2-F) 11-15 Me Me H 6-Br Ph(2-Cl) 11-16 Me Me H 6-Br Ph(2,6-F₂) 11-17Me Me H 6-Br Ph(2,6-Cl₂) 11-18 Me Me H 6-CF₃ Ph(2,6-F₂) 11-19 Me Me H6-CN Ph(2,6-F₂) 11-20 Me CN H H Ph(2,6-F₂) 11-21 Me CO₂Et H H Ph(2,6-F₂)11-22 Me CN H 6-Cl Ph(2,6-F₂) 11-23 Me CO₂Et H 6-Cl Ph(2,6-F₂) 11-24 MeEt H H Ph(2,6-F₂) 11-25 Me Me COMe H Ph(2,6-F₂) 11-26 Me Me CH₂OMe HPh(2,6-F₂) 11-27 Me Me H H 1-naphthyl 11-28 Me Me H H 2-naphthyl 11-29Me Me H H 2-thienyl 11-30 Me Me H H 3-thienyl 11-31 Me Me H H2-pyrazinyl 11-32 Me Me H H 2-pyridyl 11-33 Me Me H H 3-pyridyl 11-34 MeMe H H 4- trifluoromethyl- 3-pyridyl 11-35 Me Me H H 4-pyridyl 11-36 MeMe H H 2-furyl 11-37 Me Me H H 3-furyl 11-38 Me Me H 2-Cl Ph(2-F) 11-39Me Me H 2-Cl Ph(2,6-F₂) 11-40 Me Me H 2-Cl Ph(2-Cl) 11-41 Me Me H 2-ClPh(2-Me) 11-42 Me Me H 2-Cl Ph(2-CF₃) 11-43 Me Me H 2-Cl Ph(2-F-6-Cl)11-44 Me Me H 2-Me Ph(2-F) 11-45 Me Me H 2-Me Ph(2,6-F₂) 11-46 Me Me H2-Me Ph(2-Cl) 11-47 Me Me H 2-Me Ph(2-Me) 11-48 Me Me H 2-Me Ph(2-CF₃)11-49 Me Me H 2-Me Ph(2-F-6-Cl)

TABLE 12

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 12-1 Me Me H HPh 12-2 Me Me H H Ph(2-F) 180-183 12-3 Me Me H H Ph(2-Cl) 12-4 Me Me H HPh(2-OMe) 12-5 Me Me H H Ph(2,6-F₂) 246-250 12-6 Me Me H H Ph(2,6-Cl₂)12-7 Me Me H H Ph(2,6-OMe₂) 12-8 Me Me H 6-Cl Ph 12-9 Me Me H 6-ClPh(2-F) 12-10 Me Me H 6-Cl Ph(2-Cl) 12-11 Me Me H 6-Cl Ph(2,6-F₂) 12-12Me Me H 6-Cl Ph(2,6-Cl₂) 12-13 Me Me H 6-Br Ph 12-14 Me Me H 6-BrPh(2-F) 12-15 Me Me H 6-Br Ph(2-Cl) 12-16 Me Me H 6-Br Ph(2,6-F₂) 12-17Me Me H 6-Br Ph(2,6-Cl₂) 12-18 Me Me H 6-CF₃ Ph(2,6-F₂) 12-19 Me Me H6-CN Ph(2,6-F₂) 12-20 Me CN H H Ph(2,6-F₂) 12-21 Me CO₂Et H H Ph(2,6-F₂)12-22 Me CN H 6-Cl Ph(2,6-F₂) 12-23 Me CO₂Et H 6-Cl Ph(2,6-F₂) 12-24 MeEt H H Ph(2,6-F₂) 12-25 Me Me COMe H Ph(2,6-F₂) 12-26 Me Me CH₂OMe HPh(2,6-F₂) 12-27 Me Me H H 1-naphthyl 12-28 Me Me H H 2-naphthyl 12-29Me Me H H 2-thienyl 12-30 Me Me H H 3-thienyl 12-31 Me Me H H2-pyrazinyl 12-32 Me Me H H 2-pyridyl 12-33 Me Me H H 3-pyridyl 12-34 MeMe H H 4- trifluoromethyl- 3-pyridyl 12-35 Me Me H H 4-pyridyl 12-36 MeMe H H 2-furyl 12-37 Me Me H H 3-furyl 12-38 Me Me H 2-Cl Ph(2-F) 12-39Me Me H 2-Cl Ph(2,6-F₂) 12-40 Me Me H 2-Cl Ph(2-Cl) 12-41 Me Me H 2-ClPh(2-Me) 12-42 Me Me H 2-Cl Ph(2-CF₃) 12-43 Me Me H 2-Cl Ph(2-F-6-Cl)12-44 Me Me H 2-Me Ph(2-F) 12-45 Me Me H 2-Me Ph(2,6-F₂) 12-46 Me Me H2-Me Ph(2-Cl) 12-47 Me Me H 2-Me Ph(2-Me) 12-48 Me Me H 2-Me Ph(2-CF₃)12-49 Me Me H 2-Me Ph(2-F-6-Cl)

TABLE 13

Com- Physical pound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 13-1Me Me H H H H H Ph 13-2 Me Me H H H H H Ph(2-Cl) Oil 13-3 Me Me H H H HH Ph(4-Cl) 13-4 Me Me H H H H H Ph(2-CF₃) 164-167 13-5 Me Me H H H H HPh(4-CF₃) 13-6 Me Me H H H H H Ph(2-F) 116-121 13-7 Me Me H H H H HPh(2,6-F₂) 134-139 13-8 Me Me H H H H H Ph(2-OCF₃) 13-9 Me Me H H H H HPh(2-OCHF₂) 13-10 Me Me H H H H H Ph(2-OMe) 13-11 Me Me H H H H HPh(2,6-(OMe)₂) 13-12 Me Me H F F H H Ph(2-NO₂) 13-13 Me Me H F F H H Ph13-14 Me Me H F F H H Ph(2-Cl) 13-15 Me Me H F F H H Ph(4-Cl) 13-16 MeMe H F F H H Ph(2-CF₃) 13-17 Me Me H F F H H Ph(4-CF₃) 13-18 Me Me H F FH H Ph(2-F) 114-117 13-19 Me Me H F F H H Ph(2,6-F₂) 123-125 13-20 Me MeH F F H H Ph(2-OCF₃) 13-21 Me Me H F F H H Ph(2-OCHF₂) 13-22 Me Me H F FH H Ph(2-OMe) 13-23 Me Me H F F H H Ph(2,6-(OMe)₂) 13-24 Me Me H F F H HPh(2-NO₂) 13-25 Me Me H F F H H Ph(2-SMe) 13-26 Me Me H H H Cl H Ph(2-F)13-27 Me Me H H H Cl H Ph(2,6-F₂) 13-28 Me Me H H H Cl H Ph(2-Cl) 13-29Me Me H H H Cl H Ph(2-Me) 13-30 Me Me H H H Cl H Ph(2-CF₃) 13-31 Me Me HH H Cl H Ph(2-F-6-Cl) 13-32 Me Me H H H Me H Ph(2-F) 13-33 Me Me H H HMe H Ph(2,6-F2) 133-135 13-34 Me Me H H H Me H Ph(2-Cl) 13-35 Me Me H HH Me H Ph(2-Me) 13-36 Me Me H H H Me H Ph(2-CF₃) 13-37 Me Me H H H Me HPh(2-F-6-Cl) 13-38 Me Me H F F Cl H Ph(2-F) 13-39 Me Me H F F Cl HPh(2,6-F₂) 13-40 Me Me H F F Cl H Ph(2-Cl) 13-41 Me Me H F F Cl HPh(2-Me) 13-42 Me Me H F F Cl H Ph(2-CF₃) 13-43 Me Me H F F Cl HPh(2-F-6-Cl) 13-44 Me Me H F F Me H Ph(2-F) 105-108 13-45 Me Me H F F MeH Ph(2,6-F₂) 178-180 13-46 Me Me H F F Me H Ph(2-Cl) 13-47 Me Me H F FMe H Ph(2-Me) 13-48 Me Me H F F Me H Ph(2-CF₃) 13-49 Me Me H F F Me HPh(2-F-6-Cl) 13-50 Me Me H H H H Me Ph(2-F) 13-51 Me Me H H H H MePh(2,6-F₂) 13-52 Me Me H H H H Me Ph(2-Cl) 13-53 Me Me H H H H MePh(2-Me) 13-54 Me Me H H H H Me Ph(2-CF₃) 13-55 Me Me H H H H MePh(2-F-6-Cl) 13-56 Me Me H F F H Me Ph(2-F) 13-57 Me Me H F F H MePh(2,6-F₂) 13-58 Me Me H F F H Me Ph(2-Cl) 13-59 Me Me H F F H MePh(2-Me) 13-60 Me Me H F F H Me Ph(2-CF₃) 13-61 Me Me H F F H MePh(2-F-6-Cl) 13-62 Me Me H Me Me Me H Ph(2-F) 13-63 Me Me H Me Me Me HPh(2,6-F₂) 13-64 Me Me H Me Me Me H Ph(2-Cl) 13-65 Me Me H Me Me Me HPh(2-Me) 13-66 Me Me H Me Me Me H Ph(2-CF₃) 13-67 Me Me H Me Me Me HPh(2-F-6-Cl) 13-68 Me Me H Me Me H Me Ph(2-F) 13-69 Me Me H Me Me H MePh(2,6-F₂) 13-70 Me Me H Me Me H Me Ph(2-Cl) 13-71 Me Me H Me Me H MePh(2-Me) 13-72 Me Me H Me Me H Me Ph(2-CF₃) 13-73 Me Me H Me Me H MePh(2-F-6-Cl) 13-74 Me Me H H H H Cl Ph(2-F) 13-75 Me Me H H H H ClPh(2,6-F₂) 13-76 Me Me H H H H Cl Ph(2-Cl) 13-77 Me Me H H H H ClPh(2-Me) 13-78 Me Me H H H H Cl Ph(2-CF₃) 13-79 Me Me H H H H ClPh(2-F-6-Cl) 13-80 Me Me H F F H Cl Ph(2-F) 13-81 Me Me H F F H ClPh(2,6-F₂) 13-82 Me Me H F F H Cl Ph(2-Cl) 13-83 Me Me H F F H ClPh(2-Me) 13-84 Me Me H F F H Cl Ph(2-CF₃) 13-85 Me Me H F F H ClPh(2-F-6-Cl) 13-86 Me Me H Me Me Cl H Ph(2-F) 13-87 Me Me H Me Me Cl HPh(2,6-F₂) 13-88 Me Me H Me Me Cl H Ph(2-Cl) 13-89 Me Me H Me Me Cl HPh(2-Me) 13-90 Me Me H Me Me Cl H Ph(2-CF₃) 13-91 Me Me H Me Me Cl HPh(2-F-6-Cl) 13-92 Me Me H Me Me H Cl Ph(2-F) 13-93 Me Me H Me Me H ClPh(2,6-F₂) 13-94 Me Me H Me Me H Cl Ph(2-Cl) 13-95 Me Me H Me Me H ClPh(2-Me) 13-96 Me Me H Me Me H Cl Ph(2-CF₃) 13-97 Me Me H Me Me H ClPh(2-F-6-Cl)

TABLE 14

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 14-1 Me Me HH H Ph 14-2 Me Me H H H Ph(2-Cl) 14-3 Me Me H H H Ph(4-Cl) 14-4 Me Me HH H Ph(2-CF₃) 14-5 Me Me H H H Ph(4-CF₃) 14-6 Me Me H H H Ph(2-F) 14-7Me Me H H H Ph(2,6-F₂) 14-8 Me Me H H H Ph(2-OCF₃) 14-9 Me Me H H HPh(2-OCHF₂) 14-10 Me Me H H H Ph(2-OMe) 14-11 Me Me H H H Ph(2,6-(OMe)₂)14-12 Me Me H F F Ph(2-NO₂) 14-13 Me Me H F F Ph 14-14 Me Me H F FPh(2-Cl) 14-15 Me Me H F F Ph(4-Cl) 14-16 Me Me H F F Ph(2-CF₃) 14-17 MeMe H F F Ph(4-CF₃) 14-18 Me Me H F F Ph(2-F) 14-19 Me Me H F FPh(2,6-F₂) 14-20 Me Me H F F Ph(2-OCF₃) 14-21 Me Me H F F Ph(2-OCHF₂)14-22 Me Me H F F Ph(2-OMe) 14-23 Me Me H F F Ph(2,6-(OMe)₂) 14-24 Me MeH F F Ph(2-NO₂) 14-25 Me Me H F F Ph(2-SMe)

TABLE 15

Com- Physical pound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 15-1Me Me H H H Me H Ph(2-F) 15-2 Me Me H H H Me H Ph(2,6-F₂) 15-3 Me Me H HH Me H Ph(2-Cl) 15-4 Me Me H H H Me H Ph(2-Me) 15-5 Me Me H H H Me HPh(2-CF₃) 15-6 Me Me H H H Me H Ph(2-F-6-Cl) 15-7 Me Me H H H H MePh(2-F) 15-8 Me Me H H H H Me Ph(2,6-F₂) 15-9 Me Me H H H H Me Ph(2-Cl)15-10 Me Me H H H H Me Ph(2-Me) 15-11 Me Me H H H H Me Ph(2-CF₃) 15-12Me Me H H H H Me Ph(2-F-6-Cl) 15-13 Me Me H Me H H H Ph(2-F) 15-14 Me MeH Me H H H Ph(2,6-F₂) 15-15 Me Me H Me H H H Ph(2-Cl) 15-16 Me Me H Me HH H Ph(2-Me) 15-17 Me Me H Me H H H Ph(2-CF₃) 15-18 Me Me H Me H H HPh(2-F-6-Cl) 15-19 Me Me H Me H Me H Ph(2-F) 15-20 Me Me H Me H Me HPh(2,6-F₂) 15-21 Me Me H Me H Me H Ph(2-Cl) 15-22 Me Me H Me H Me HPh(2-Me) 15-23 Me Me H Me H Me H Ph(2-CF₃) 15-24 Me Me H Me H Me HPh(2-F-6-Cl) 15-25 Me Me H Me H H Me Ph(2-F) 15-26 Me Me H Me H H MePh(2,6-F₂) 15-27 Me Me H Me H H Me Ph(2-Cl) 15-28 Me Me H Me H H MePh(2-Me) 15-29 Me Me H Me H H Me Ph(2-CF₃) 15-30 Me Me H Me H H MePh(2-F-6-Cl) 15-31 Me Me H H Me H H Ph(2-F) 15-32 Me Me H H Me H HPh(2,6-F₂) 15-33 Me Me H H Me H H Ph(2-Cl) 15-34 Me Me H H Me H HPh(2-Me) 15-35 Me Me H H Me H H Ph(2-CF₃) 15-36 Me Me H H Me H HPh(2-F-6-Cl) 15-37 Me Me H H Me Me H Ph(2-F) 15-38 Me Me H H Me Me HPh(2,6-F₂) 15-39 Me Me H H Me Me H Ph(2-Cl) 15-40 Me Me H H Me Me HPh(2-Me) 15-41 Me Me H H Me Me H Ph(2-CF₃) 15-42 Me Me H H Me Me HPh(2-F-6-Cl) 15-43 Me Me H H Me H Me Ph(2-F) 15-44 Me Me H H Me H MePh(2,6-F₂) 15-45 Me Me H H Me H Me Ph(2-Cl) 15-46 Me Me H H Me H MePh(2-Me) 15-47 Me Me H H Me H Me Ph(2-CF₃) 15-48 Me Me H H Me H MePh(2-F-6-Cl) 15-49 Me Me H H H Cl H Ph(2-F) 15-50 Me Me H H H Cl HPh(2,6-F₂) 15-51 Me Me H H H Cl H Ph(2-Cl) 15-52 Me Me H H H Cl HPh(2-Me) 15-53 Me Me H H H Cl H Ph(2-CF₃) 15-54 Me Me H H H Cl HPh(2-F-6-Cl) 15-55 Me Me H H H H Cl Ph(2-F) 15-56 Me Me H H H H ClPh(2,6-F₂) 15-57 Me Me H H H H Cl Ph(2-Cl) 15-58 Me Me H H H H ClPh(2-Me) 15-59 Me Me H H H H Cl Ph(2-CF₃) 15-60 Me Me H H H H ClPh(2-F-6-Cl) 15-61 Me Me H Cl H H H Ph(2-F) 15-62 Me Me H Cl H H HPh(2,6-F₂) 15-63 Me Me H Cl H H H Ph(2-Cl) 15-64 Me Me H Cl H H HPh(2-Me) 15-65 Me Me H Cl H H H Ph(2-CF₃) 15-66 Me Me H Cl H H HPh(2-F-6-Cl) 15-67 Me Me H Me H Cl H Ph(2-F) 15-68 Me Me H Me H Cl HPh(2,6-F₂) 15-69 Me Me H Me H Cl H Ph(2-Cl) 15-70 Me Me H Me H Cl HPh(2-Me) 15-71 Me Me H Me H Cl H Ph(2-CF₃) 15-72 Me Me H Me H Cl HPh(2-F-6-Cl) 15-73 Me Me H Me H H Cl Ph(2-F) 15-74 Me Me H Me H H ClPh(2,6-F₂) 15-75 Me Me H Me H H Cl Ph(2-Cl) 15-76 Me Me H Me H H ClPh(2-Me) 15-77 Me Me H Me H H Cl ph(2-CF₃) 15-78 Me Me H Me H H Clph(2-F-6-Cl) 15-79 Me Me H H Cl H H Ph(2-F) 15-80 Me Me H H Cl H HPh(2,6-F₂) 15-81 Me Me H H Cl H H Ph(2-Cl) 15-82 Me Me H H Cl H HPh(2-Me) 15-83 Me Me H H Cl H H Ph(2-CF₃) 15-84 Me Me H H Cl H HPh(2-F-6-Cl) 15-85 Me Me H H Me Cl H Ph(2-F) 15-86 Me Me H H Me Cl HPh(2,6-F₂) 15-87 Me Me H H Me Cl H Ph(2-Cl) 15-88 Me Me H H Me Cl HPh(2-Me) 15-89 Me Me H H Me Cl H Ph(2-CF₃) 15-90 Me Me H H Me Cl HPh(2-F-6-Cl) 15-91 Me Me H H Me H Cl Ph(2-F) 15-92 Me Me H H Me H ClPh(2,6-F₂) 15-93 Me Me H H Me H Cl Ph(2-Cl) 15-94 Me Me H H Me H ClPh(2-Me) 15-95 Me Me H H Me H Cl Ph(2-CF₃) 15-96 Me Me H H Me H ClPh(2-F-6-Cl)

TABLE 16

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 16-1 Me Me H H F Me H Ph(2-F) 16-2  Me Me H H F Me H Ph(2,6-F₂) 16-3  Me Me HH F Me H Ph(2-Cl) 16-4  Me Me H H F Me H Ph(2-Me) 16-5  Me Me H H F Me HPh(2-CF₃) 16-6  Me Me H H F Me H Ph(2-F-6-Cl) 16-7  Me Me H H F H MePh(2-F) 16-8  Me Me H H F H Me Ph(2,6-F₂) 16-9  Me Me H H F H MePh(2-Cl) 16-10 Me Me H H F H Me Ph(2-Me) 16-11 Me Me H H F H MePh(2-CF₃) 16-12 Me Me H H F H Me Ph(2-F-6-Cl) 16-13 Me Me H F H H HPh(2-F) 16-14 Me Me H F H H H Ph(2,6-F₂) 16-15 Me Me H F H H H Ph(2-Cl)16-16 Me Me H F H H H Ph(2-Me) 16-17 Me Me H F H H H Ph(2-CF₃) 16-18 MeMe H F H H H Ph(2-F-6-Cl) 16-19 Me Me H F H Me H Ph(2-F) 16-20 Me Me H FH Me H Ph(2,6-F₂) 16-21 Me Me H F H Me H Ph(2-Cl) 16-22 Me Me H F H Me HPh(2-Me) 16-23 Me Me H F H Me H Ph(2-CF₃) 16-24 Me Me H F H Me HPh(2-F-6-Cl) 16-25 Me Me H F H H Me Ph(2-F) 16-26 Me Me H F H H MePh(2,6-F₂) 16-27 Me Me H F H H Me Ph(2-Cl) 16-28 Me Me H F H H MePh(2-Me) 16-29 Me Me H F H H Me Ph(2-CF₃) 16-30 Me Me H F H H MePh(2-F-6-Cl) 16-31 Me Me H F F H H Ph(2-F) 16-32 Me Me H F F H HPh(2,6-F₂) 125-128 16-33 Me Me H F F H H Ph(2-Cl) 16-34 Me Me H F F H HPh(2-Me) 16-35 Me Me H F F H H Ph(2-CF₃) 16-36 Me Me H F F H HPh(2-F-6-Cl) 16-37 Me Me H F F Me H Ph(2-F) 110-112 16-38 Me Me H F F MeH Ph(2,6-F₂) 128-130 16-39 Me Me H F F Me H Ph(2-Cl) 16-40 Me Me H F FMe H Ph(2-Me) 16-41 Me Me H F F Me H Ph(2-CF₃) 16-42 Me Me H F F Me HPh(2-F-6-Cl) 16-43 Me Me H F F H Me Ph(2-F) 16-44 Me Me H F F H MePh(2,6-F₂) 16-45 Me Me H F F H Me Ph(2-Cl) 16-46 Me Me H F F H MePh(2-Me) 16-47 Me Me H F F H Me Ph(2-CF₃) 16-48 Me Me H F F H MePh(2-F-6-Cl) 16-49 Me Me H H F Cl H Ph(2-F) 16-50 Me Me H H F Cl HPh(2,6-F₂) 16-51 Me Me H H F Cl H Ph(2-Cl) 16-52 Me Me H H F Cl HPh(2-Me) 16-53 Me Me H H F Cl H Ph(2-CF₃) 16-54 Me Me H H F Cl HPh(2-F-6-Cl) 16-55 Me Me H H F H Cl Ph(2-F) 16-56 Me Me H H F H ClPh(2,6-F₂) 16-57 Me Me H H F H Cl Ph(2-Cl) 16-58 Me Me H H F H ClPh(2-Me) 16-59 Me Me H H F H Cl Ph(2-CF₃) 16-60 Me Me H H F H ClPh(2-F-6-Cl) 16-61 Me Me H F H Cl H Ph(2-F) 16-62 Me Me H F H Cl HPh(2,6-F₂) 16-63 Me Me H F H Cl H Ph(2-Cl) 16-64 Me Me H F H Cl HPh(2-Me) 16-65 Me Me H F H Cl H Ph(2-CF₃) 16-66 Me Me H F H Cl HPh(2-F-6-Cl) 16-67 Me Me H F H H Cl Ph(2-F) 16-68 Me Me H F H H ClPh(2,6-F₂) 16-69 Me Me H F H H Cl Ph(2-Cl) 16-70 Me Me H F H H ClPh(2-Me) 16-71 Me Me H F H H Cl Ph(2-CF₃) 16-72 Me Me H F H H ClPh(2-F-6-Cl) 16-73 Me Me H F F Cl H Ph(2-F) 16-74 Me Me H F F Cl HPh(2,6-F₂) 16-75 Me Me H F F Cl H Ph(2-Cl) 16-76 Me Me H F F Cl HPh(2-Me) 16-77 Me Me H F F Cl H Ph(2-CF₃) 16-78 Me Me H F F Cl HPh(2-F-6-Cl) 16-79 Me Me H F F H Cl Ph(2-F) 16-80 Me Me H F F H ClPh(2,6-F₂) 16-81 Me Me H F F H Cl Ph(2-Cl) 16-82 Me Me H F F H ClPh(2-Me) 16-83 Me Me H F F H Cl Ph(2-CF₃) 16-84 Me Me H F F H ClPh(2-F-6-Cl)

TABLE 17

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 17-1 Me Me H F H H H Ph(2-F) 17-2  Me Me H F H H H Ph(2,6-F₂) 17-3  Me Me H FH H H Ph(2-Cl) 17-4  Me Me H F H H H Ph(2-Me) 17-5  Me Me H F H H HPh(2-CF₃) 17-6  Me Me H F H H H Ph(2-F-6-Cl) 17-7  Me Me H F H Me HPh(2-F) 17-8  Me Me H F H Me H Ph(2,6-F₂) 17-9  Me Me H F H Me HPh(2-Cl) 17-10 Me Me H F H Me H Ph(2-Me) 17-11 Me Me H F H Me HPh(2-CF₃) 17-12 Me Me H F H Me H Ph(2-F-6-Cl) 17-13 Me Me H F Cl H HPh(2-F) 17-14 Me Me H F Cl H H Ph(2,6-F₂) 17-15 Me Me H F Cl H HPh(2-Cl) 17-16 Me Me H F Cl H H Ph(2-Me) 17-17 Me Me H F Cl H HPh(2-CF₃) 17-18 Me Me H F Cl H H Ph(2-F-6-Cl) 17-19 Me Me H F Cl Me HPh(2-F) 17-20 Me Me H F Cl Me H Ph(2,6-F₂) 17-21 Me Me H F Cl Me HPh(2-Cl) 17-22 Me Me H F Cl Me H Ph(2-Me) 17-23 Me Me H F Cl Me HPh(2-CF₃) 17-24 Me Me H F Cl Me H Ph(2-F-6-Cl) 17-25 Me Me H H F H HPh(2-F) 17-26 Me Me H H F H H Ph(2,6-F₂) 17-27 Me Me H H F H H Ph(2-Cl)17-28 Me Me H H F H H Ph(2-Me) 17-29 Me Me H H F H H Ph(2-CF₃) 17-30 MeMe H H F H H Ph(2-F-6-Cl) 17-31 Me Me H H F Me H Ph(2-F) 17-32 Me Me H HF Me H Ph(2,6-F₂) 17-33 Me Me H H F Me H Ph(2-Cl) 17-34 Me Me H H F Me HPh(2-Me) 17-35 Me Me H H F Me H Ph(2-CF₃) 17-36 Me Me H H F Me HPh(2-F-6-Cl) 17-37 Me Me H Cl F H H Ph(2-F) 17-38 Me Me H Cl F H HPh(2,6-F₂) 17-39 Me Me H Cl F H H Ph(2-Cl) 17-40 Me Me H Cl F H HPh(2-Me) 17-41 Me Me H Cl F H H Ph(2-CF₃) 17-42 Me Me H Cl F H HPh(2-F-6-Cl) 17-43 Me Me H Cl F Me H Ph(2-F) 17-44 Me Me H Cl F Me HPh(2,6-F₂) 17-45 Me Me H Cl F Me H Ph(2-Cl) 17-46 Me Me H Cl F Me HPh(2-Me) 17-47 Me Me H Cl F Me H Ph(2-CF₃) 17-48 Me Me H Cl F Me HPh(2-F-6-Cl) 17-49 Me Me H F H Cl H Ph(2-F) 17-50 Me Me H F H Cl HPh(2,6-F₂) 17-51 Me Me H F H Cl H Ph(2-Cl) 17-52 Me Me H F H Cl HPh(2-Me) 17-53 Me Me H F H Cl H Ph(2-CF₃) 17-54 Me Me H F H Cl HPh(2-F-6-Cl) 17-55 Me Me H F Cl Cl H Ph(2-F) 17-56 Me Me H F Cl Cl HPh(2,6-F₂) 17-57 Me Me H F Cl Cl H Ph(2-Cl) 17-58 Me Me H F Cl Cl HPh(2-Me) 17-59 Me Me H F Cl Cl H Ph(2-CF₃) 17-60 Me Me H F Cl Cl HPh(2-F-6-Cl) 17-61 Me Me H H F Cl H Ph(2-F) 17-62 Me Me H H F Cl HPh(2,6-F₂) 17-63 Me Me H H F Cl H Ph(2-Cl) 17-64 Me Me H H F Cl HPh(2-Me) 17-65 Me Me H H F Cl H Ph(2-CF₃) 17-66 Me Me H H F Cl HPh(2-F-6-Cl) 17-67 Me Me H Cl F Cl H Ph(2-F) 17-68 Me Me H Cl F Cl HPh(2,6-F₂) 17-69 Me Me H Cl F Cl H Ph(2-Cl) 17-70 Me Me H Cl F Cl HPh(2-Me) 17-71 Me Me H Cl F Cl H Ph(2-CF₃) 17-72 Me Me H Cl F Cl HPh(2-F-6-Cl)

TABLE 18

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 18-1 Me Me H H H H H Ph(2-F) 18-2  Me Me H H H H H Ph(2,6-F₂) 18-3  Me Me H HH H H Ph(2-Cl) 18-4  Me Me H H H H H Ph(2-Me) 18-5  Me Me H H H H HPh(2-CF₃) 18-6  Me Me H H H H H Ph(2-F-6-Cl) 18-7  Me Me H H H Me HPh(2-F) 18-8  Me Me H H H Me H Ph(2,6-F₂) 18-9  Me Me H H H Me HPh(2-Cl) 18-10 Me Me H H H Me H Ph(2-Me) 18-11 Me Me H H H Me HPh(2-CF₃) 18-12 Me Me H H H Me H Ph(2-F-6-Cl) 18-13 Me Me H F H H HPh(2-F) 18-14 Me Me H F H H H Ph(2,6-F₂) 18-15 Me Me H F H H H Ph(2-Cl)18-16 Me Me H F H H H Ph(2-Me) 18-17 Me Me H F H H H Ph(2-CF₃) 18-18 MeMe H F H H H Ph(2-F-6-Cl) 18-19 Me Me H F H Me H Ph(2-F) 18-20 Me Me H FH Me H Ph(2,6-F₂) 18-21 Me Me H F H Me H Ph(2-Cl) 18-22 Me Me H F H Me HPh(2-Me) 18-23 Me Me H F H Me H Ph(2-CF₃) 18-24 Me Me H F H Me HPh(2-F-6-Cl) 18-25 Me Me H F H H Me Ph(2-F) 18-26 Me Me H F H H MePh(2,6-F₂) 18-27 Me Me H F H H Me Ph(2-Cl) 18-28 Me Me H F H H MePh(2-Me) 18-29 Me Me H F H H Me Ph(2-CF₃) 18-30 Me Me H F H H MePh(2-F-6-Cl) 18-31 Me Me H F F H H Ph(2-F) 18-32 Me Me H F F H HPh(2,6-F₂) 18-33 Me Me H F F H H Ph(2-Cl) 18-34 Me Me H F F H H Ph(2-Me)18-35 Me Me H F F H H Ph(2-CF₃) 18-36 Me Me H F F H H Ph(2-F-6-Cl) 18-37Me Me H F F Me H Ph(2-F) 18-38 Me Me H F F Me H Ph(2,6-F₂) 18-39 Me Me HF F Me H Ph(2-Cl) 18-40 Me Me H F F Me H Ph(2-Me) 18-41 Me Me H F F Me HPh(2-CF₃) 18-42 Me Me H F F Me H Ph(2-F-6-Cl) 18-43 Me Me H F F H MePh(2-F) 18-44 Me Me H F F H Me Ph(2,6-F₂) 18-45 Me Me H F F H MePh(2-Cl) 18-46 Me Me H F F H Me Ph(2-Me) 18-47 Me Me H F F H MePh(2-CF₃) 18-48 Me Me H F F H Me Ph(2-F-6-Cl)

TABLE 19

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 19-1  Me MeH H H Ph(2-F) 19-2  Me Me H H H Ph(2,6-F₂) 19-3  Me Me H H H Ph(2-Cl)19-4  Me Me H H H Ph(2-Me) 19-5  Me Me H H H Ph(2-CF₃) 19-6  Me Me H H HPh(2-F-6-Cl) 19-7  Me Me H H Cl Ph(2-F) 19-8  Me Me H H Cl Ph(2,6-F₂)19-9  Me Me H H Cl Ph(2-Cl) 19-10 Me Me H H Cl Ph(2-Me) 19-11 Me Me H HCl Ph(2-CF₃) 19-12 Me Me H H Cl Ph(2-F-6-Cl) 19-13 Me Me H H Me Ph(2-F)19-14 Me Me H H Me Ph(2,6-F₂) 19-15 Me Me H H Me Ph(2-Cl) 19-16 Me Me HH Me Ph(2-Me) 19-17 Me Me H H Me Ph(2-CF₃) 19-18 Me Me H H MePh(2-F-6-Cl) 19-19 Me Me H H OMe Ph(2-F) 19-20 Me Me H H OMe Ph(2,6-F₂)19-21 Me Me H H OMe Ph(2-Cl) 19-22 Me Me H H OMe Ph(2-Me) 19-23 Me Me HH OMe Ph(2-CF₃) 19-24 Me Me H H OMe Ph(2-F-6-Cl) 19-25 Me Me H F HPh(2-F) 19-26 Me Me H F H Ph(2,6-F₂) 19-27 Me Me H F H Ph(2-Cl) 19-28 MeMe H F H Ph(2-Me) 19-29 Me Me H F H Ph(2-CF₃) 19-30 Me Me H F HPh(2-F-6-Cl) 19-31 Me Me H F Cl Ph(2-F) 19-32 Me Me H F Cl Ph(2,6-F₂)19-33 Me Me H F Cl Ph(2-Cl) 19-34 Me Me H F Cl Ph(2-Me) 19-35 Me Me H FCl Ph(2-CF₃) 19-36 Me Me H F Cl Ph(2-F-6-Cl) 19-37 Me Me H F Me Ph(2-F)19-38 Me Me H F Me Ph(2,6-F₂) 19-39 Me Me H F Me Ph(2-Cl) 19-40 Me Me HF Me Ph(2-Me) 19-41 Me Me H F Me Ph(2-CF₃) 19-42 Me Me H F MePh(2-F-6-Cl) 19-43 Me Me H F OMe Ph(2-F) 19-44 Me Me H F OMe Ph(2,6-F₂)19-45 Me Me H F OMe Ph(2-Cl) 19-46 Me Me H F OMe Ph(2-Me) 19-47 Me Me HF OMe Ph(2-CF₃) 19-48 Me Me H F OMe Ph(2-F-6-Cl) 19-49 Me Me H H BrPh(2-F) 19-50 Me Me H H Br Ph(2,6-F₂) 19-51 Me Me H H Br Ph(2-Cl) 19-52Me Me H H Br Ph(2-Me) 19-53 Me Me H H Br Ph(2-CF₃) 19-54 Me Me H H BrPh(2-F-6-Cl) 19-55 Me Me H H CF₃ Ph(2-F) 19-56 Me Me H H CF₃ Ph(2,6-F₂)19-57 Me Me H H CF₃ Ph(2-Cl) 19-58 Me Me H H CF₃ Ph(2-Me) 19-59 Me Me HH CF₃ Ph(2-CF₃) 19-60 Me Me H H CF₃ Ph(2-F-6-Cl) 19-61 Me Me H H OCF₃Ph(2-F) 19-62 Me Me H H OCF₃ Ph(2,6-F₂) 19-63 Me Me H H OCF₃ Ph(2-Cl)19-64 Me Me H H OCF₃ Ph(2-Me) 19-65 Me Me H H OCF₃ Ph(2-CF₃) 19-66 Me MeH H OCF₃ Ph(2-F-6-Cl) 19-67 Me Me H H OCH₂CF₃ Ph(2-F) 19-68 Me Me H HOCH₂CF₃ Ph(2,6-F₂) 19-69 Me Me H H OCH₂CF₃ Ph(2-Cl) 19-70 Me Me H HOCH₂CF₃ Ph(2-Me) 19-71 Me Me H H OCH₂CF₃ Ph(2-CF₃) 19-72 Me Me H HOCH₂CF₃ Ph(2-F-6-Cl) 19-73 Me Me H H OCHF₂ Ph(2-F) 19-74 Me Me H H OCHF₂Ph(2,6-F₂) 19-75 Me Me H H OCHF₂ Ph(2-Cl) 19-76 Me Me H H OCHF₂ Ph(2-Me)19-77 Me Me H H OCHF₂ Ph(2-CF₃) 19-78 Me Me H H OCHF₂ Ph(2-F-6-Cl) 19-79Me Me H F Br Ph(2-F) 19-80 Me Me H F Br Ph(2,6-F₂) 19-81 Me Me H F BrPh(2-Cl) 19-82 Me Me H F Br Ph(2-Me) 19-83 Me Me H F Br Ph(2-CF₃) 19-84Me Me H F Br Ph(2-F-6-Cl) 19-85 Me Me H F CF₃ Ph(2-F) 19-86 Me Me H FCF₃ Ph(2,6-F₂) 19-87 Me Me H F CF₃ Ph(2-Cl) 19-88 Me Me H F CF₃ Ph(2-Me)19-89 Me Me H F CF₃ Ph(2-CF₃) 19-90 Me Me H F CF₃ Ph(2-F-6-Cl) 19-91 MeMe H F OCF₃ Ph(2-F) 19-92 Me Me H F OCF₃ Ph(2,6-F₂) 19-93 Me Me H F OCF₃Ph(2-Cl) 19-94 Me Me H F OCF₃ Ph(2-Me) 19-95 Me Me H F OCF₃ Ph(2-CF₃)19-96 Me Me H F OCF₃ Ph(2-F-6-Cl) 19-97 Me Me H F OCH₂CF₃ Ph(2-F) 19-98Me Me H F OCH₂CF₃ Ph(2,6-F₂) 19-99 Me Me H F OCH₂CF₃ Ph(2-Cl)  19-100 MeMe H F OCH₂CF₃ Ph(2-Me)  19-101 Me Me H F OCH₂CF₃ Ph(2-CF₃)  19-102 MeMe H F OCH₂CF₃ Ph(2-F-6-Cl)  19-103 Me Me H F OCHF₂ Ph(2-F)  19-104 MeMe H F OCHF₂ Ph(2,6-F₂)  19-105 Me Me H F OCHF₂ Ph(2-Cl)  19-106 Me Me HF OCHF₂ Ph(2-Me)  19-107 Me Me H F OCHF₂ Ph(2-CF₃)  19-108 Me Me H FOCHF₂ Ph(2-F-6-Cl)

TABLE 20

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 20-1  Me MeH H H Ph(2-F) 20-2  Me Me H H H Ph(2,6-F₂) 20-3  Me Me H H H Ph(2-Cl)20-4  Me Me H H H Ph(2-Me) 20-5  Me Me H H H Ph(2-CF₃) 20-6  Me Me H H HPh(2-F-6-Cl) 20-7  Me Me H H Cl Ph(2-F) 20-8  Me Me H H Cl Ph(2,6-F₂)20-9  Me Me H H Cl Ph(2-Cl) 20-10 Me Me H H Cl Ph(2-Me) 20-11 Me Me H HCl Ph(2-CF₃) 20-12 Me Me H H Cl Ph(2-F-6-Cl) 20-13 Me Me H H Me Ph(2-F)20-14 Me Me H H Me Ph(2,6-F₂) 20-15 Me Me H H Me Ph(2-Cl) 20-16 Me Me HH Me Ph(2-Me) 20-17 Me Me H H Me Ph(2-CF₃) 20-18 Me Me H H MePh(2-F-6-Cl) 20-19 Me Me H H OMe Ph(2-F) 20-20 Me Me H H OMe Ph(2,6-F₂)20-21 Me Me H H OMe Ph(2-Cl) 20-22 Me Me H H OMe Ph(2-Me) 20-23 Me Me HH OMe Ph(2-CF₃) 20-24 Me Me H H OMe Ph(2-F-6-Cl) 20-25 Me Me H F HPh(2-F) 20-26 Me Me H F H Ph(2,6-F₂) 20-27 Me Me H F H Ph(2-Cl) 20-28 MeMe H F H Ph(2-Me) 20-29 Me Me H F H Ph(2-CF₃) 20-30 Me Me H F HPh(2-F-6-Cl) 20-31 Me Me H F Cl Ph(2-F) 20-32 Me Me H F Cl Ph(2,6-F₂)20-33 Me Me H F Cl Ph(2-Cl) 20-34 Me Me H F Cl Ph(2-Me) 20-35 Me Me H FCl Ph(2-CF₃) 20-36 Me Me H F Cl Ph(2-F-6-Cl) 20-37 Me Me H F Me Ph(2-F)20-38 Me Me H F Me Ph(2,6-F₂) 20-39 Me Me H F Me Ph(2-Cl) 20-40 Me Me HF Me Ph(2-Me) 20-41 Me Me H F Me Ph(2-CF₃) 20-42 Me Me H F MePh(2-F-6-Cl) 20-43 Me Me H F OMe Ph(2-F) 20-44 Me Me H F OMe Ph(2,6-F₂)20-45 Me Me H F OMe Ph(2-Cl) 20-46 Me Me H F OMe Ph(2-Me) 20-47 Me Me HF OMe Ph(2-CF₃) 20-48 Me Me H F OMe Ph(2-F-6-Cl) 20-49 Me Me H H BrPh(2-F) 20-50 Me Me H H Br Ph(2,6-F₂) 20-51 Me Me H H Br Ph(2-Cl) 20-52Me Me H H Br Ph(2-Me) 20-53 Me Me H H Br Ph(2-CF₃) 20-54 Me Me H H BrPh(2-F-6-Cl) 20-55 Me Me H H CF₃ Ph(2-F) 20-56 Me Me H H CF₃ Ph(2,6-F₂)20-57 Me Me H H CF₃ Ph(2-Cl) 20-58 Me Me H H CF₃ Ph(2-Me) 20-59 Me Me HH CF₃ Ph(2-CF₃) 20-60 Me Me H H CF₃ Ph(2-F-6-Cl) 20-61 Me Me H H OCF₃Ph(2-F) 20-62 Me Me H H OCF₃ Ph(2,6-F₂) 20-63 Me Me H H OCF₃ Ph(2-Cl)20-64 Me Me H H OCF₃ Ph(2-Me) 20-65 Me Me H H OCF₃ Ph(2-CF₃) 20-66 Me MeH H OCF₃ Ph(2-F-6-Cl) 20-67 Me Me H H OCH₂CF₃ Ph(2-F) 20-68 Me Me H HOCH₂CF₃ Ph(2,6-F₂) 20-69 Me Me H H OCH₂CF₃ Ph(2-Cl) 20-70 Me Me H HOCH₂CF₃ Ph(2-Me) 20-71 Me Me H H OCH₂CF₃ Ph(2-CF₃) 20-72 Me Me H HOCH₂CF₃ Ph(2-F-6-Cl) 20-73 Me Me H H OCHF₂ Ph(2-F) 20-74 Me Me H H OCHF₂Ph(2,6-F₂) 20-75 Me Me H H OCHF₂ Ph(2-Cl) 20-76 Me Me H H OCHF₂ Ph(2-Me)20-77 Me Me H H OCHF₂ Ph(2-CF₃) 20-78 Me Me H H OCHF₂ Ph(2-F-6-Cl) 20-79Me Me H F Br Ph(2-F) 20-80 Me Me H F Br Ph(2,6-F₂) 20-81 Me Me H F BrPh(2-Cl) 20-82 Me Me H F Br Ph(2-Me) 20-83 Me Me H F Br Ph(2-CF₃) 20-84Me Me H F Br Ph(2-F-6-Cl) 20-85 Me Me H F CF₃ Ph(2-F) 20-86 Me Me H FCF₃ Ph(2,6-F₂) 20-87 Me Me H F CF₃ Ph(2-Cl) 20-88 Me Me H F CF₃ Ph(2-Me)20-89 Me Me H F CF₃ Ph(2-CF₃) 20-90 Me Me H F CF₃ Ph(2-F-6-Cl) 20-91 MeMe H F OCF₃ Ph(2-F) 20-92 Me Me H F OCF₃ Ph(2,6-F₂) 20-93 Me Me H F OCF₃Ph(2-Cl) 20-94 Me Me H F OCF₃ Ph(2-Me) 20-95 Me Me H F OCF₃ Ph(2-CF₃)20-96 Me Me H F OCF₃ Ph(2-F-6-Cl) 20-97 Me Me H F OCH₂CF₃ Ph(2-F) 20-98Me Me H F OCH₂CF₃ Ph(2,6-F₂) 20-99 Me Me H F OCH₂CF₃ Ph(2-Cl)  20-100 MeMe H F OCH₂CF₃ Ph(2-Me)  20-101 Me Me H F OCH₂CF₃ Ph(2-CF₃)  20-102 MeMe H F OCH₂CF₃ Ph(2-F-6-Cl)  20-103 Me Me H F OCHF₂ Ph(2-F)  20-104 MeMe H F OCHF₂ Ph(2,6-F₂)  20-105 Me Me H F OCHF₂ Ph(2-Cl)  20-106 Me Me HF OCHF₂ Ph(2-Me)  20-107 Me Me H F OCHF₂ Ph(2-CF₃)  20-108 Me Me H FOCHF₂ Ph(2-F-6-Cl)

TABLE 21

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 21-1 Me Me H H H H H Ph(2-F) 21-2  Me Me H H H H H Ph(2,6-F₂) 21-3  Me Me H HH H H Ph(2-Cl) 21-4  Me Me H H H H H Ph(2-Me) 21-5  Me Me H H H H HPh(2-CF₃) 21-6  Me Me H H H H H Ph(2-F-6-Cl) 21-7  Me Me H H H Cl HPh(2-F) 21-8  Me Me H H H Cl H Ph(2,6-F₂) 21-9  Me Me H H H Cl HPh(2-Cl) 21-10 Me Me H H H Cl H Ph(2-Me) 21-11 Me Me H H H Cl HPh(2-CF₃) 21-12 Me Me H H H Cl H Ph(2-F-6-Cl) 21-13 Me Me H H H Me HPh(2-F) 21-14 Me Me H H H Me H Ph(2,6-F₂) 21-15 Me Me H H H Me HPh(2-Cl) 21-16 Me Me H H H Me H Ph(2-Me) 21-17 Me Me H H H Me HPh(2-CF₃) 21-18 Me Me H H H Me H Ph(2-F-6-Cl) 21-19 Me Me H H H H MePh(2-F) 21-20 Me Me H H H H Me Ph(2,6-F₂) 21-21 Me Me H H H H MePh(2-Cl) 21-22 Me Me H H H H Me Ph(2-Me) 21-23 Me Me H H H H MePh(2-CF₃) 21-24 Me Me H H H H Me Ph(2-F-6-Cl) 21-25 Me Me H F F H HPh(2-F) 21-26 Me Me H F F H H Ph(2,6-F₂) 21-27 Me Me H F F H H Ph(2-Cl)21-28 Me Me H F F H H Ph(2-Me) 21-29 Me Me H F F H H Ph(2-CF₃) 21-30 MeMe H F F H H Ph(2-F-6-Cl) 21-31 Me Me H F F Cl H Ph(2-F) 21-32 Me Me H FF Cl H Ph(2,6-F₂) 21-33 Me Me H F F Cl H Ph(2-Cl) 21-34 Me Me H F F Cl HPh(2-Me) 21-35 Me Me H F F Cl H Ph(2-CF₃) 21-36 Me Me H F F Cl HPh(2-F-6-Cl) 21-37 Me Me H F F Me H Ph(2-F) 21-38 Me Me H F F Me HPh(2,6-F₂) 21-39 Me Me H F F Me H Ph(2-Cl) 21-40 Me Me H F F Me HPh(2-Me) 21-41 Me Me H F F Me H Ph(2-CF₃) 21-42 Me Me H F F Me HPh(2-F-6-Cl) 21-43 Me Me H F F H Me Ph(2-F) 21-44 Me Me H F F H MePh(2,6-F₂) 21-45 Me Me H F F H Me Ph(2-Cl) 21-46 Me Me H F F H MePh(2-Me) 21-47 Me Me H F F H Me Ph(2-CF₃) 21-48 Me Me H F F H MePh(2-F-6-Cl) 21-49 Me Me H Me H H H Ph(2-F) 21-50 Me Me H Me H H HPh(2,6-F₂) 21-51 Me Me H Me H H H Ph(2-Cl) 21-52 Me Me H Me H H HPh(2-Me) 21-53 Me Me H Me H H H Ph(2-CF₃) 21-54 Me Me H Me H H HPh(2-F-6-Cl) 21-55 Me Me H Me H Me H Ph(2-F) 21-56 Me Me H Me H Me HPh(2,6-F₂) 21-57 Me Me H Me H Me H Ph(2-Cl) 21-58 Me Me H Me H Me HPh(2-Me) 21-59 Me Me H Me H Me H Ph(2-CF₃) 21-60 Me Me H Me H Me HPh(2-F-6-Cl) 21-61 Me Me H Me H H Me Ph(2-F) 21-62 Me Me H Me H H MePh(2,6-F₂) 21-63 Me Me H Me H H Me Ph(2-Cl) 21-64 Me Me H Me H H MePh(2-Me) 21-65 Me Me H Me H H Me Ph(2-CF₃) 21-66 Me Me H Me H H MePh(2-F-6-Cl) 21-67 Me Me H F H H H Ph(2-F) 21-68 Me Me H F H H HPh(2,6-F₂) 21-69 Me Me H F H H H Ph(2-Cl) 21-70 Me Me H F H H H Ph(2-Me)21-71 Me Me H F H H H Ph(2-CF₃) 21-72 Me Me H F H H H Ph(2-F-6-Cl) 21-73Me Me H H F H H Ph(2-F) 21-74 Me Me H H F H H Ph(2,6-F₂) 21-75 Me Me H HF H H Ph(2-Cl) 21-76 Me Me H H F H H Ph(2-Me) 21-77 Me Me H H F H HPh(2-CF₃) 21-78 Me Me H H F H H Ph(2-F-6-Cl) 21-79 Me Me H F H Me HPh(2-F) 21-80 Me Me H F H Me H Ph(2,6-F₂) 21-81 Me Me H F H Me HPh(2-Cl) 21-82 Me Me H F H Me H Ph(2-Me) 21-83 Me Me H F H Me HPh(2-CF₃) 21-84 Me Me H F H Me H Ph(2-F-6-Cl) 21-85 Me Me H H F Me HPh(2-F) 21-86 Me Me H H F Me H Ph(2,6-F₂) 21-87 Me Me H H F Me HPh(2-Cl) 21-88 Me Me H H F Me H Ph(2-Me) 21-89 Me Me H H F Me HPh(2-CF₃) 21-90 Me Me H H F Me H Ph(2-F-6-Cl) 21-91 Me Me H F H H MePh(2-F) 21-92 Me Me H F H H Me Ph(2,6-F₂) 21-93 Me Me H F H H MePh(2-Cl) 21-94 Me Me H F H H Me Ph(2-Me) 21-95 Me Me H F H H MePh(2-CF₃) 21-96 Me Me H F H H Me Ph(2-F-6-Cl) 21-97 Me Me H H F H MePh(2-F) 21-98 Me Me H H F H Me Ph(2,6-F₂) 21-99 Me Me H H F H MePh(2-Cl)  21-100 Me Me H H F H Me Ph(2-Me)  21-101 Me Me H H F H MePh(2-CF₃)  21-102 Me Me H H F H Me Ph(2-F-6-Cl)  21-103 Me Me H F H Cl HPh(2-F)  21-104 Me Me H F H Cl H Ph(2,6-F₂)  21-105 Me Me H F H Cl HPh(2-Cl)  21-106 Me Me H F H Cl H Ph(2-Me)  21-107 Me Me H F H Cl HPh(2-CF₃)  21-108 Me Me H F H Cl H Ph(2-F-6-Cl)  21-109 Me Me H H F Cl HPh(2-F)  21-110 Me Me H H F Cl H Ph(2,6-F₂)  21-111 Me Me H H F Cl HPh(2-Cl)  21-112 Me Me H H F Cl H Ph(2-Me)  21-113 Me Me H H F Cl HPh(2-CF₃)  21-114 Me Me H H F Cl H Ph(2-F-6-Cl)  21-115 Me Me H F H H ClPh(2-F)  21-116 Me Me H F H H Cl Ph(2,6-F₂)  21-117 Me Me H F H H ClPh(2-Cl)  21-118 Me Me H F H H Cl Ph(2-Me)  21-119 Me Me H F H H ClPh(2-CF₃)  21-120 Me Me H F H H Cl Ph(2-F-6-Cl)  21-121 Me Me H H F H ClPh(2-F)  21-122 Me Me H H F H Cl Ph(2,6-F₂)  21-123 Me Me H H F H ClPh(2-Cl)  21-124 Me Me H H F H Cl Ph(2-Me)  21-125 Me Me H H F H ClPh(2-CF₃)  21-126 Me Me H H F H Cl Ph(2-F-6-Cl)  21-127 Me Me H Me H ClH Ph(2-F)  21-128 Me Me H Me H Cl H Ph(2,6-F₂)  21-129 Me Me H Me H Cl HPh(2-Cl)  21-130 Me Me H Me H Cl H Ph(2-Me)  21-131 Me Me H Me H Cl HPh(2-CF₃)  21-132 Me Me H Me H Cl H Ph(2-F-6-Cl)  21-133 Me Me H Me H HCl Ph(2-F)  21-134 Me Me H Me H H Cl Ph(2,6-F₂)  21-135 Me Me H Me H HCl Ph(2-Cl)  21-136 Me Me H Me H H Cl Ph(2-Me)  21-137 Me Me H Me H H ClPh(2-CF₃)  21-138 Me Me H Me H H Cl Ph(2-F-6-Cl)

TABLE 22

Phys1cal Compound propert1es No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 22-1 Me Me H Me H H H Ph(2-F) 22-2  Me Me H Me H H H Ph(2,6-F₂) 22-3  Me Me HMe H H H Ph(2-Cl) 22-4  Me Me H Me H H H Ph(2-Me) 22-5  Me Me H Me H H HPh(2-CF₃) 22-6  Me Me H Me H H H Ph(2-F-6-Cl) 22-7  Me Me H Me H Cl HPh(2-F) 22-8  Me Me H Me H Cl H Ph(2,6-F₂) 22-9  Me Me H Me H Cl HPh(2-Cl) 22-10 Me Me H Me H Cl H Ph(2-Me) 22-11 Me Me H Me H Cl HPh(2-CF₃) 22-12 Me Me H Me H Cl H Ph(2-F-6-Cl) 22-13 Me Me H Me H Me HPh(2-F) 22-14 Me Me H Me H Me H Ph(2,6-F₂) 22-15 Me Me H Me H Me HPh(2-Cl) 22-16 Me Me H Me H Me H Ph(2-Me) 22-17 Me Me H Me H Me HPh(2-CF₃) 22-18 Me Me H Me H Me H Ph(2-F-6-Cl) 22-19 Me Me H Me H H MePh(2-F) 22-20 Me Me H Me H H Me Ph(2,6-F₂) 22-21 Me Me H Me H H MePh(2-Cl) 22-22 Me Me H Me H H Me Ph(2-Me) 22-23 Me Me H Me H H MePh(2-CF₃) 22-24 Me Me H Me H H Me Ph(2-F-6-Cl) 22-25 Me Me H H Me H HPh(2-F) 22-26 Me Me H H Me H H Ph(2,6-F₂) 22-27 Me Me H H Me H HPh(2-Cl) 22-28 Me Me H H Me H H Ph(2-Me) 22-29 Me Me H H Me H HPh(2-CF₃) 22-30 Me Me H H Me H H Ph(2-F-6-Cl) 22-31 Me Me H H Me Cl HPh(2-F) 22-32 Me Me H H Me Cl H Ph(2,6-F₂) 22-33 Me Me H H Me Cl HPh(2-Cl) 22-34 Me Me H H Me Cl H Ph(2-Me) 22-35 Me Me H H Me Cl HPh(2-CF₃) 22-36 Me Me H H Me Cl H Ph(2-F-6-Cl) 22-37 Me Me H H Me Me HPh(2-F) 22-38 Me Me H H Me Me H Ph(2,6-F₂) 22-39 Me Me H H Me Me HPh(2-Cl) 22-40 Me Me H H Me Me H Ph(2-Me) 22-41 Me Me H H Me Me HPh(2-CF₃) 22-42 Me Me H H Me Me H Ph(2-F-6-Cl) 22-43 Me Me H H Me H MePh(2-F) 22-44 Me Me H H Me H Me Ph(2,6-F₂) 22-45 Me Me H H Me H MePh(2-Cl) 22-46 Me Me H H Me H Me Ph(2-Me) 22-47 Me Me H H Me H MePh(2-CF₃) 22-48 Me Me H H Me H Me Ph(2-F-6-Cl)

TABLE 23

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 23-1 Me Me H H H H H Ph(2-F) 23-1  Me Me H H H H H Ph(2-F) 23-2  Me Me H H HH H Ph(2,6-F₂) 23-3  Me Me H H H H H Ph(2-Cl) 23-4  Me Me H H H H HPh(2-Me) 23-5  Me Me H H H H H Ph(2-CF₃) 23-6  Me Me H H H H HPh(2-F-6-Cl) 23-7  Me Me H H H Cl H Ph(2-F) 23-8  Me Me H H H Cl HPh(2,6-F₂) 23-9  Me Me H H H Cl H Ph(2-Cl) 23-10 Me Me H H H Cl HPh(2-Me) 23-11 Me Me H H H Cl H Ph(2-CF₃) 23-12 Me Me H H H Cl HPh(2-F-6-Cl) 23-13 Me Me H H H Me H Ph(2-F) 23-14 Me Me H H H Me HPh(2,6-F₂) 23-15 Me Me H H H Me H Ph(2-Cl) 23-16 Me Me H H H Me HPh(2-Me) 23-17 Me Me H H H Me H Ph(2-CF₃) 23-18 Me Me H H H Me HPh(2-F-6-Cl) 23-19 Me Me H H H H Me Ph(2-F) 23-20 Me Me H H H H MePh(2,6-F₂) 23-21 Me Me H H H H Me Ph(2-Cl) 23-22 Me Me H H H H MePh(2-Me) 23-23 Me Me H H H H Me Ph(2-CF₃) 23-24 Me Me H H H H MePh(2-F-6-Cl) 23-25 Me Me H F F H H Ph(2-F) 23-26 Me Me H F F H HPh(2,6-F₂) 23-27 Me Me H F F H H Ph(2-Cl) 23-28 Me Me H F F H H Ph(2-Me)23-29 Me Me H F F H H Ph(2-CF₃) 23-30 Me Me H F F H H Ph(2-F-6-Cl) 23-31Me Me H F F Cl H Ph(2-F) 23-32 Me Me H F F Cl H Ph(2,6-F₂) 23-33 Me Me HF F Cl H Ph(2-Cl) 23-34 Me Me H F F Cl H Ph(2-Me) 23-35 Me Me H F F Cl HPh(2-CF₃) 23-36 Me Me H F F Cl H Ph(2-F-6-Cl) 23-37 Me Me H F F Me HPh(2-F) 23-38 Me Me H F F Me H Ph(2,6-F₂) 23-39 Me Me H F F Me HPh(2-Cl) 23-40 Me Me H F F Me H Ph(2-Me) 23-41 Me Me H F F Me HPh(2-CF₃) 23-42 Me Me H F F Me H Ph(2-F-6-Cl) 23-43 Me Me H F F H MePh(2-F) 23-44 Me Me H F F H Me Ph(2,6-F₂) 23-45 Me Me H F F H MePh(2-Cl) 23-46 Me Me H F F H Me Ph(2-Me) 23-47 Me Me H F F H MePh(2-CF₃) 23-48 Me Me H F F H Me Ph(2-F-6-Cl) 23-49 Me Me H H H H ClPh(2-F) 23-50 Me Me H H H H Cl Ph(2,6-F₂) 23-51 Me Me H H H H ClPh(2-Cl) 23-52 Me Me H H H H Cl Ph(2-Me) 23-53 Me Me H H H H ClPh(2-CF₃) 23-54 Me Me H H H H Cl Ph(2-F-6-Cl) 23-55 Me Me H F F H ClPh(2-F) 23-56 Me Me H F F H Cl Ph(2,6-F₂) 23-57 Me Me H F F H ClPh(2-Cl) 23-58 Me Me H F F H Cl Ph(2-Me) 23-59 Me Me H F F H ClPh(2-CF₃) 23-60 Me Me H F F H Cl Ph(2-F-6-Cl) 23-61 Me Me H F H Cl HPh(2-F) 23-62 Me Me H F H Cl H Ph(2,6-F₂) 23-63 Me Me H F H Cl HPh(2-Cl) 23-64 Me Me H F H Cl H Ph(2-Me) 23-65 Me Me H F H Cl HPh(2-CF₃) 23-66 Me Me H F H Cl H Ph(2-F-6-Cl) 23-67 Me Me H H F Cl HPh(2-F) 23-68 Me Me H H F Cl H Ph(2,6-F₂) 23-69 Me Me H H F Cl HPh(2-Cl) 23-70 Me Me H H F Cl H Ph(2-Me) 23-71 Me Me H H F Cl HPh(2-CF₃) 23-72 Me Me H H F Cl H Ph(2-F-6-Cl) 23-73 Me Me H F H Me HPh(2-F) 23-74 Me Me H F H Me H Ph(2,6-F₂) 23-75 Me Me H F H Me HPh(2-Cl) 23-76 Me Me H F H Me H Ph(2-Me) 23-77 Me Me H F H Me HPh(2-CF₃) 23-78 Me Me H F H Me H Ph(2-F-6-Cl) 23-79 Me Me H H F Me HPh(2-F) 23-80 Me Me H H F Me H Ph(2,6-F₂) 23-81 Me Me H H F Me HPh(2-Cl) 23-82 Me Me H H F Me H Ph(2-Me) 23-83 Me Me H H F Me HPh(2-CF₃) 23-84 Me Me H H F Me H Ph(2-F-6-Cl) 23-85 Me Me H F H H ClPh(2-F) 23-86 Me Me H F H H Cl Ph(2,6-F₂) 23-87 Me Me H F H H ClPh(2-Cl) 23-88 Me Me H F H H Cl Ph(2-Me) 23-89 Me Me H F H H ClPh(2-CF₃) 23-90 Me Me H F H H Cl Ph(2-F-6-Cl) 23-91 Me Me H H F H MePh(2-F) 23-92 Me Me H H F H Me Ph(2,6-F₂) 23-93 Me Me H H F H MePh(2-Cl) 23-94 Me Me H H F H Me Ph(2-Me) 23-95 Me Me H H F H MePh(2-CF₃) 23-96 Me Me H H F H Me Ph(2-F-6-Cl) 23-97 Me Me H F H H MePh(2-F) 23-98 Me Me H F H H Me Ph(2,6-F₂) 23-99 Me Me H F H H MePh(2-Cl)  23-100 Me Me H F H H Me Ph(2-Me)  23-101 Me Me H F H H MePh(2-CF₃)  23-102 Me Me H F H H Me Ph(2-F-6-Cl)  23-103 Me Me H H F H MePh(2-F)  23-104 Me Me H H F H Me Ph(2,6-F₂)  23-105 Me Me H H F H MePh(2-Cl)  23-106 Me Me H H F H Me Ph(2-Me)  23-107 Me Me H H F H MePh(2-CF₃)  23-108 Me Me H H F H Me Ph(2-F-6-Cl)

TABLE 24

Com- Physical pound properties No. R₁ R₂ R₃ X₁ X₂ X₃ X₄ B (mp ° C.) 24-1Me Me H H H H H Ph(2-F) 24-2 Me Me H H H H H Ph(2,6-F₂) 24-3 Me Me H H HH H Ph(2-Cl) 24-4 Me Me H H H H H Ph(2-Me) 24-5 Me Me H H H H HPh(2-CF₃) 24-6 Me Me H H H H H Ph(2-F-6-Cl) 24-7 Me Me H H H H MePh(2-F) 24-8 Me Me H H H H Me Ph(2,6-F₂) 24-9 Me Me H H H H Me Ph(2-Cl)24-10 Me Me H H H H Me Ph(2-Me) 24-11 Me Me H H H H Me Ph(2-CF₃) 24-12Me Me H H H H Me Ph(2-F-6-Cl) 24-13 Me Me H F H H H Ph(2-F) 24-14 Me MeH F H H H Ph(2,6-F₂) 24-15 Me Me H F H H H Ph(2-Cl) 24-16 Me Me H F H HH Ph(2-Me) 24-17 Me Me H F H H H Ph(2-CF₃) 24-18 Me Me H F H H HPh(2-F-6-Cl) 24-19 Me Me H F H H Me Ph(2-F) 24-20 Me Me H F H H MePh(2,6-F₂) 24-21 Me Me H F H H Me Ph(2-Cl) 24-22 Me Me H F H H MePh(2-Me) 24-23 Me Me H F H H Me Ph(2-CF₃) 24-24 Me Me H F H H MePh(2-F-6-Cl) 24-25 Me Me H H F H H Ph(2-F) 24-26 Me Me H H F H HPh(2,6-F₂) 24-27 Me Me H H F H H Ph(2-Cl) 24-28 Me Me H H F H H Ph(2-Me)24-29 Me Me H H F H H Ph(2-CF₃) 24-30 Me Me H H F H H Ph(2-F-6-Cl) 24-31Me Me H H F H Me Ph(2-F) 24-32 Me Me H H F H Me Ph(2,6-F₂) 24-33 Me Me HH F H Me Ph(2-Cl) 24-34 Me Me H H F H Me Ph(2-Me) 24-35 Me Me H H F H MePh(2-CF₃) 24-36 Me Me H H F H Me Ph(2-F-6-Cl) 24-37 Me Me H F F H HPh(2-F) 24-38 Me Me H F F H H Ph(2,6-F₂) 24-39 Me Me H F F H H Ph(2-Cl)24-40 Me Me H F F H H Ph(2-Me) 24-41 Me Me H F F H H Ph(2-CF₃) 24-42 MeMe H F F H H Ph(2-F-6-Cl) 24-43 Me Me H F F H Me Ph(2-F) 24-44 Me Me H FF H Me Ph(2,6-F₂) 24-45 Me Me H F F H Me Ph(2-Cl) 24-46 Me Me H F F H MePh(2-Me) 24-47 Me Me H F F H Me Ph(2-CF₃) 24-48 Me Me H F F H MePh(2-F-6-Cl) 24-49 Me Me H H H Me Me Ph(2-F) 24-50 Me Me H H H Me MePh(2,6-F₂) 24-51 Me Me H H H Me Me Ph(2-Cl) 24-52 Me Me H H H Me MePh(2-Me) 24-53 Me Me H H H Me Me Ph(2-CF₃) 24-54 Me Me H H H Me MePh(2-F-6-Cl) 24-55 Me Me H H H OMe Me Ph(2-F) 24-56 Me Me H H H OMe MePh(2,6-F₂) 24-57 Me Me H H H OMe Me Ph(2-Cl) 24-58 Me Me H H H OMe MePh(2-Me) 24-59 Me Me H H H OMe Me Ph(2-CF₃) 24-60 Me Me H H H OMe MePh(2-F-6-Cl) 24-61 Me Me H H H OH Me Ph(2-F) 24-62 Me Me H H H OH MePh(2,6-F₂) 24-63 Me Me H H H OH Me Ph(2-Cl) 24-64 Me Me H H H OH MePh(2-Me) 24-65 Me Me H H H OH Me Ph(2-CF₃) 24-66 Me Me H H H OH MePh(2-F-6-Cl) 24-67 Me Me H Me H H Me Ph(2-F) 24-68 Me Me H Me H H MePh(2,6-F₂) 24-69 Me Me H Me H H Me Ph(2-Cl) 24-70 Me Me H Me H H MePh(2-Me) 24-71 Me Me H Me H H Me Ph(2-CF₃) 24-72 Me Me H Me H H MePh(2-F-6-Cl) 24-73 Me Me H H H H Cl Ph(2-F) 24-74 Me Me H H H H ClPh(2,6-F₂) 24-75 Me Me H H H H Cl Ph(2-Cl) 24-76 Me Me H H H H ClPh(2-Me) 24-77 Me Me H H H H Cl Ph(2-CF₃) 24-78 Me Me H H H H ClPh(2-F-6-Cl) 24-79 Me Me H F H H Cl Ph(2-F) 24-80 Me Me H F H H ClPh(2,6-F₂) 24-81 Me Me H F H H Cl Ph(2-Cl) 24-82 Me Me H F H H ClPh(2-Me) 24-83 Me Me H F H H Cl Ph(2-CF₃) 24-84 Me Me H F H H ClPh(2-F-6-Cl) 24-85 Me Me H H F H Cl Ph(2-F) 24-86 Me Me H H F H ClPh(2,6-F₂) 24-87 Me Me H H F H Cl Ph(2-Cl) 24-88 Me Me H H F H ClPh(2-Me) 24-89 Me Me H H F H Cl Ph(2-CF₃) 24-90 Me Me H H F H ClPh(2-F-6-Cl) 24-91 Me Me H F F H Cl Ph(2-F) 24-92 Me Me H F F H ClPh(2,6-F₂) 24-93 Me Me H F F H Cl Ph(2-Cl) 24-94 Me Me H F F H ClPh(2-Me) 24-95 Me Me H F F H Cl Ph(2-CF₃) 24-96 Me Me H F F H ClPh(2-F-6-Cl) 24-97 Me Me H H H Me Cl Ph(2-F) 24-98 Me Me H H H Me ClPh(2,6-F₂) 24-99 Me Me H H H Me Cl Ph(2-Cl) 24-100 Me Me H H H Me ClPh(2-Me) 24-101 Me Me H H H Me Cl Ph(2-CF₃) 24-102 Me Me H H H Me ClPh(2-F-6-Cl) 24-103 Me Me H H H OMe Cl Ph(2-F) 24-104 Me Me H H H OMe ClPh(2,6-F₂) 24-105 Me Me H H H OMe Cl Ph(2-Cl) 24-106 Me Me H H H OMe ClPh(2-Me) 24-107 Me Me H H H OMe Cl Ph(2-CF₃) 24-108 Me Me H H H ONe ClPh(2-F-6-Cl) 24-109 Me Me H H H OH Cl Ph(2-F) 24-110 Me Me H H H OH ClPh(2,6-F₂) 24-111 Me Me H H H OH Cl Ph(2-Cl) 24-112 Me Me H H H OH ClPh(2-Me) 24-113 Me Me H H H OH Cl Ph(2-CF₃) 24-114 Me Me H H H OH ClPh(2-F-6-Cl) 24-115 Me Me H Me H H Cl Ph(2-F) 24-116 Me Me H Me H H ClPh(2,6-F₂) 24-117 Me Me H Me H H Cl Ph(2-Cl) 24-118 Me Me H Me H H ClPh(2-Me) 24-119 Me Me H Me H H Cl Ph(2-CF₃) 24-120 Me Me H Me H H ClPh(2-F-6-Cl)

TABLE 25

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 25-1 Me Me HH H Ph(2-F) 25-2 Me Me H H H Ph(2,6-F₂) 25-3 Me Me H H H Ph(2-Cl) 25-4Me Me H H H Ph(2-Me) 25-5 Me Me H H H Ph(2-CF₃) 25-6 Me Me H H HPh(2-F-6-Cl) 25-7 Me Me H Cl H Ph(2-F) 25-8 Me Me H Cl H Ph(2,6-F₂) 25-9Me Me H Cl H Ph(2-Cl) 25-10 Me Me H Cl H Ph(2-Me) 25-11 Me Me H Cl HPh(2-CF₃) 25-12 Me Me H Cl H Ph(2-F-6-Cl) 25-13 Me Me H Me H Ph(2-F)25-14 Me Me H Me H Ph(2,6-F₂) 25-15 Me Me H Me H Ph(2-Cl) 25-16 Me Me HMe H Ph(2-Me) 25-17 Me Me H Me H Ph(2-CF₃) 25-18 Me Me H Me HPh(2-F-6-Cl) 25-19 Me Me H H Cl Ph(2-F) 25-20 Me Me H H Cl Ph(2,6-F₂)25-21 Me Me H H Cl Ph(2-Cl) 25-22 Me Me H H Cl Ph(2-Me) 25-23 Me Me H HCl Ph(2-CF₃) 25-24 Me Me H H Cl Ph(2-F-6-Cl) 25-25 Me Me H H Me Ph(2-F)25-26 Me Me H H Me Ph(2,6-F₂) 25-27 Me Me H H Me Ph(2-Cl) 25-28 Me Me HH Me Ph(2-Me) 25-29 Me Me H H Me Ph(2-CF₃) 25-30 Me Me H H MePh(2-F-6-Cl) 25-31 Me Me H Me Me Ph(2-F) 25-32 Me Me H Me Me Ph(2,6-F₂)25-33 Me Me H Me Me Ph(2-Cl) 25-34 Me Me H Me Me Ph(2-Me) 25-35 Me Me HMe Me Ph(2-CF₃) 25-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 26

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 26-1 Me Me HH H Ph(2-F) 26-2 Me Me H H H Ph(2,6-F₂) 26-3 Me Me H H H Ph(2-Cl) 26-4Me Me H H H Ph(2-Me) 26-5 Me Me H H H Ph(2-CF₃) 26-6 Me Me H H HPh(2-F-6-Cl) 26-7 Me Me H Cl H Ph(2-F) 26-8 Me Me H Cl H Ph(2,6-F₂) 26-9Me Me H Cl H Ph(2-Cl) 26-10 Me Me H Cl H Ph(2-Me) 26-11 Me Me H Cl HPh(2-CF₃) 26-12 Me Me H Cl H Ph(2-F-6-Cl) 26-13 Me Me H Me H Ph(2-F)26-14 Me Me H Me H Ph(2,6-F₂) 26-15 Me Me H Me H Ph(2-Cl) 26-16 Me Me HMe H Ph(2-Me) 26-17 Me Me H Me H Ph(2-CF₃) 26-18 Me Me H Me HPh(2-F-6-Cl) 26-19 Me Me H H Cl Ph(2-F) 26-20 Me Me H H Cl Ph(2,6-F₂)26-21 Me Me H H Cl Ph(2-Cl) 26-22 Me Me H H Cl Ph(2-Me) 26-23 Me Me H HCl Ph(2-CF₃) 26-24 Me Me H H Cl Ph(2-F-6-Cl) 26-25 Me Me H H Me Ph(2-F)26-26 Me Me H H Me Ph(2,6-F₂) 26-27 Me Me H H Me Ph(2-Cl) 26-28 Me Me HH Me Ph(2-Me) 26-29 Me Me H H Me Ph(2-CF₃) 26-30 Me Me H H MePh(2-F-6-Cl) 26-31 Me Me H Me Me Ph(2-F) 26-32 Me Me H Me Me Ph(2,6-F₂)26-33 Me Me H Me Me Ph(2-Cl) 26-34 Me Me H Me Me Ph(2-Me) 26-35 Me Me HMe Me Ph(2-CF₃) 26-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 27

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 27-1 Me Me HH H Ph(2-F) 27-2 Me Me H H H Ph(2,6-F₂) 27-3 Me Me H H H Ph(2-Cl) 27-4Me Me H H H Ph(2-Me) 27-5 Me Me H H H Ph(2-CF₃) 27-6 Me Me H H HPh(2-F-6-Cl) 27-7 Me Me H Cl H Ph(2-F) 27-8 Me Me H Cl H Ph(2,6-F₂) 27-9Me Me H Cl H Ph(2-Cl) 27-10 Me Me H Cl H Ph(2-Me) 27-11 Me Me H Cl HPh(2-CF₃) 27-12 Me Me H Cl H Ph(2-F-6-Cl) 27-13 Me Me H Me H Ph(2-F)27-14 Me Me H Me H Ph(2,6-F₂) 27-15 Me Me H Me H Ph(2-Cl) 27-16 Me Me HMe H Ph(2-Me) 27-17 Me Me H Me H Ph(2-CF₃) 27-18 Me Me H Me HPh(2-F-6-Cl) 27-19 Me Me H H Cl Ph(2-F) 27-20 Me Me H H Cl Ph(2,6-F₂)27-21 Me Me H H Cl Ph(2-Cl) 27-22 Me Me H H Cl Ph(2-Me) 27-23 Me Me H HCl Ph(2-CF₃) 27-24 Me Me H H Cl Ph(2-F-6-Cl) 27-25 Me Me H H Me Ph(2-F)27-26 Me Me H H Me Ph(2,6-F₂) 27-27 Me Me H H Me Ph(2-Cl) 27-28 Me Me HH Me Ph(2-Me) 27-29 Me Me H H Me Ph(2-CF₃) 27-30 Me Me H H MePh(2-F-6-Cl) 27-31 Me Me H Me Me Ph(2-F) 27-32 Me Me H Me Me Ph(2,6-F₂)27-33 Me Me H Me Me Ph(2-Cl) 27-34 Me Me H Me Me Ph(2-Me) 27-35 Me Me HMe Me Ph(2-CF₃) 27-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 28

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 28-1 Me Me HH H Ph(2-F) 28-2 Me Me H H H Ph(2,6-F₂) 28-3 Me Me H H H Ph(2-Cl) 28-4Me Me H H H Ph(2-Me) 28-5 Me Me H H H Ph(2-CF₃) 28-6 Me Me H H HPh(2-F-6-Cl) 28-7 Me Me H Cl H Ph(2-F) 28-8 Me Me H Cl H Ph(2,6-F₂) 28-9Me Me H Cl H Ph(2-Cl) 28-10 Me Me H Cl H Ph(2-Me) 28-11 Me Me H Cl HPh(2-CF₃) 28-12 Me Me H Cl H Ph(2-F-6-Cl) 28-13 Me Me H Me H Ph(2-F)28-14 Me Me H Me H Ph(2,6-F₂) 28-15 Me Me H Me H Ph(2-Cl) 28-16 Me Me HMe H Ph(2-Me) 28-17 Me Me H Me H Ph(2-CF₃) 28-18 Me Me H Me HPh(2-F-6-Cl) 28-19 Me Me H H Cl Ph(2-F) 28-20 Me Me H H Cl Ph(2,6-F₂)28-21 Me Me H H Cl Ph(2-Cl) 28-22 Me Me H H Cl Ph(2-Me) 28-23 Me Me H HCl Ph(2-CF₃) 28-24 Me Me H H Cl Ph(2-F-6-Cl) 28-25 Me Me H H Me Ph(2-F)28-26 Me Me H H Me Ph(2,6-F₂) 28-27 Me Me H H Me Ph(2-Cl) 28-28 Me Me HH Me Ph(2-Me) 28-29 Me Me H H Me Ph(2-CF₃) 28-30 Me Me H H MePh(2-F-6-Cl) 28-31 Me Me H Me Me Ph(2-F) 28-32 Me Me H Me Me Ph(2,6-F₂)28-33 Me Me H Me Me Ph(2-Cl) 28-34 Me Me H Me Me Ph(2-Me) 28-35 Me Me HMe Me Ph(2-CF₃) 28-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 29

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 29-1 Me Me HH H Ph(2-F) 29-2 Me Me H H H Ph(2,6-F₂) 29-3 Me Me H H H Ph(2-Cl) 29-4Me Me H H H Ph(2-Me) 29-5 Me Me H H H Ph(2-CF₃) 29-6 Me Me H H HPh(2-F-6-Cl) 29-7 Me Me H Cl H Ph(2-F) 29-8 Me Me H Cl H Ph(2,6-F₂) 29-9Me Me H Cl H ph(2-Cl) 29-10 Me Me H Cl H ph(2-Me) 29-11 Me Me H Cl HPh(2-CF₃) 29-12 Me Me H Cl H Ph(2-F-6-Cl) 29-13 Me Me H Me H Ph(2-F)29-14 Me Me H Me H Ph(2,6-F₂) 29-15 Me Me H Me H Ph(2-Cl) 29-16 Me Me HMe H Ph(2-Me) 29-17 Me Me H Me H Ph(2-CF₃) 29-18 Me Me H Me HPh(2-F-6-Cl) 29-19 Me Me H H Cl Ph(2-F) 29-20 Me Me H H Cl Ph(2,6-F₂)29-21 Me Me H H Cl Ph(2-Cl) 29-22 Me Me H H Cl Ph(2-Me) 29-23 Me Me H HCl Ph(2-CF₃) 29-24 Me Me H H Cl Ph(2-F-6-Cl) 29-25 Me Me H H Me Ph(2-F)29-26 Me Me H H Me Ph(2,6-F₂) 29-27 Me Me H H Me Ph(2-Cl) 29-28 Me Me HH Me Ph(2-Me) 29-29 Me Me H H Me Ph(2-CF₃) 29-30 Me Me H H MePh(2-F-6-Cl) 29-31 Me Me H Me Me Ph(2-F) 29-32 Me Me H Me Me Ph(2,6-F₂)29-33 Me Me H Me Me Ph(2-Cl) 29-34 Me Me H Me Me Ph(2-Me) 29-35 Me Me HMe Me Ph(2-CF₃) 29-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 30

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 30-1 Me Me HH H Ph(2-F) 30-2 Me Me H H H Ph(2,6-F₂) 30-3 Me Me H H H Ph(2-Cl) 30-4Me Me H H H Ph(2-Me) 30-5 Me Me H H H Ph(2-CF₃) 30-6 Me Me H H HPh(2-F-6-Cl) 30-7 Me Me H Cl H Ph(2-F) 30-8 Me Me H Cl H Ph(2,6-F₂) 30-9Me Me H Cl H Ph(2-Cl) 30-10 Me Me H Cl H Ph(2-Me) 30-11 Me Me H Cl HPh(2-CF₃) 30-12 Me Me H Cl H Ph(2-F-6-Cl) 30-13 Me Me H Me H Ph(2-F)30-14 Me Me H Me H Ph(2,6-F₂) 30-15 Me Me H Me H Ph(2-Cl) 30-16 Me Me HMe H Ph(2-Me) 30-17 Me Me H Me H Ph(2-CF₃) 30-18 Me Me H Me HPh(2-F-6-Cl) 30-19 Me Me H H Cl Ph(2-F) 30-20 Me Me H H Cl Ph(2,6-F₂)30-21 Me Me H H Cl Ph(2-Cl) 30-22 Me Me H H Cl Ph(2-Me) 30-23 Me Me H HCl Ph(2-CF₃) 30-24 Me Me H H Cl Ph(2-F-6-Cl) 30-25 Me Me H H Me Ph(2-F)30-26 Me Me H H Me Ph(2,6-F₂) 30-27 Me Me H H Me Ph(2-Cl) 30-28 Me Me HH Me Ph(2-Me) 30-29 Me Me H H Me Ph(2-CF₃) 30-30 Me Me H H MePh(2-F-6-Cl) 30-31 Me Me H Me Me Ph(2-F) 30-32 Me Me H Me Me Ph(2,6-F₂)30-33 Me Me H Me Me Ph(2-Cl) 30-34 Me Me H Me Me Ph(2-Me) 30-35 Me Me HMe Me Ph(2-CF₃) 30-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 31

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 31-1 Me Me HH H Ph(2-F) 31-2 Me Me H H H Ph(2,6-F₂) 31-3 Me Me H H H Ph(2-Cl) 31-4Me Me H H H Ph(2-Me) 31-5 Me Me H H H Ph(2-CF₃) 31-6 Me Me H H HPh(2-F-6-Cl) 31-7 Me Me H Cl H Ph(2-F) 31-8 Me Me H Cl H Ph(2,6-F₂) 31-9Me Me H Cl H Ph(2-Cl) 31-10 Me Me H Cl H Ph(2-Me) 31-11 Me Me H Cl HPh(2-CF₃) 31-12 Me Me H Cl H Ph(2-F-6-Cl) 31-13 Me Me H Me H Ph(2-F)31-14 Me Me H Me H Ph(2,6-F₂) 31-15 Me Me H Me H Ph(2-Cl) 31-16 Me Me HMe H Ph(2-Me) 31-17 Me Me H Me H Ph(2-CF₃) 31-18 Me Me H Me HPh(2-F-6-Cl) 31-19 Me Me H H Cl Ph(2-F) 31-20 Me Me H H Cl Ph(2,6-F₂)31-21 Me Me H H Cl Ph(2-Cl) 31-22 Me Me H H Cl Ph(2-Me) 31-23 Me Me H HCl Ph(2-CF₃) 31-24 Me Me H H Cl Ph(2-F-6-Cl) 31-25 Me Me H H Me Ph(2-F)31-26 Me Me H H Me Ph(2,6-F₂) 31-27 Me Me H H Me Ph(2-Cl) 31-28 Me Me HH Me Ph(2-Me) 31-29 Me Me H H Me Ph(2-CF₃) 31-30 Me Me H H MePh(2-F-6-Cl) 31-31 Me Me H Me Me Ph(2-F) 31-32 Me Me H Me Me Ph(2,6-F₂)31-33 Me Me H Me Me Ph(2-Cl) 31-34 Me Me H Me Me Ph(2-Me) 31-35 Me Me HMe Me Ph(2-CF₃) 31-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 32

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ (mp ° C.) 32-1 Me Me H HH Ph(2-F) 32-2 Me Me H H H Ph(2,6-F₂) 32-3 Me Me H H H Ph(2-Cl) 32-4 MeMe H H H Ph(2-Me) 32-5 Me Me H H H Ph(2-CF₃) 32-6 Me Me H H HPh(2-F-6-Cl) 32-7 Me Me H Cl H Ph(2-F) 32-8 Me Me H Cl H Ph(2,6-F₂) 32-9Me Me H Cl H Ph(2-Cl) 32-10 Me Me H Cl H Ph(2-Me) 32-11 Me Me H Cl HPh(2-CF₃) 32-12 Me Me H Cl H Ph(2-F-6-Cl) 32-13 Me Me H Me H Ph(2-F)32-14 Me Me H Me H Ph(2,6-F₂) 32-15 Me Me H Me H Ph(2-Cl) 32-16 Me Me HMe H Ph(2-Me) 32-17 Me Me H Me H Ph(2-CF₃) 32-18 Me Me H Me HPh(2-F-6-Cl) 32-19 Me Me H H Cl Ph(2-F) 32-20 Me Me H H Cl Ph(2,6-F₂)32-21 Me Me H H Cl Ph(2-Cl) 32-22 Me Me H H Cl Ph(2-Me) 32-23 Me Me H HCl Ph(2-CF₃) 32-24 Me Me H H Cl Ph(2-F-6-Cl) 32-25 Me Me H H Me Ph(2-F)32-26 Me Me H H Me Ph(2,6-F₂) 32-27 Me Me H H Me Ph(2-Cl) 32-28 Me Me HH Me Ph(2-Me) 32-29 Me Me H H Me Ph(2-CF₃) 32-30 Me Me H H MePh(2-F-6-Cl) 32-31 Me Me H Me Me Ph(2-F) 32-32 Me Me H Me Me Ph(2,6-F₂)32-33 Me Me H Me Me Ph(2-Cl) 32-34 Me Me H Me Me Ph(2-Me) 32-35 Me Me HMe Me Ph(2-CF₃) 32-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 33

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 33-1 Me Me H HPh(2-F) 33-2 Me Me H H Ph(2,6-F₂) 33-3 Me Me H H Ph(2-Cl) 33-4 Me Me H HPh(2-Me) 33-5 Me Me H H Ph(2-CF₃) 33-6 Me Me H H Ph(2-F-6-Cl) 33-7 Me MeH Cl Ph(2-F) 33-8 Me Me H Cl Ph(2,6-F₂) 33-9 Me Me H Cl Ph(2-Cl) 33-10Me Me H Cl Ph(2-Me) 33-11 Me Me H Cl Ph(2-CF₃) 33-12 Me Me H ClPh(2-F-6-Cl) 33-13 Me Me H Br Ph(2-F) 33-14 Me Me H Br Ph(2,6-F₂) 33-15Me Me H Br Ph(2-Cl) 33-16 Me Me H Br Ph(2-Me) 33-17 Me Me H Br Ph(2-CF₃)33-18 Me Me H Br Ph(2-F-6-Cl) 33-19 Me Me H Me Ph(2-F) 33-20 Me Me H MePh(2,6-F₂) 33-21 Me Me H Me Ph(2-Cl) 33-22 Me Me H Me Ph(2-Me) 33-23 MeMe H Me Ph(2-CF₃) 33-24 Me Me H Me Ph(2-F-6-Cl) 33-25 Me Me H Et Ph(2-F)33-26 Me Me H Et Ph(2,6-F₂) 33-27 Me Me H Et Ph(2-Cl) 33-28 Me Me H EtPh(2-Me) 33-29 Me Me H Et Ph(2-CF₃) 33-30 Me Me H Et Ph(2-F-6-Cl)

TABLE 34

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 34-1 Me Me H HPh(2-F) 34-2 Me Me H H Ph(2,6-F₂) 34-3 Me Me H H Ph(2-Cl) 34-4 Me Me H HPh(2-Me) 34-5 Me Me H H Ph(2-CF₃) 34-6 Me Me H H Ph(2-F-6-Cl) 34-7 Me MeH Cl Ph(2-F) 34-8 Me Me H Cl Ph(2,6-F₂) 34-9 Me Me H Cl Ph(2-Cl) 34-10Me Me H Cl Ph(2-Me) 34-11 Me Me H Cl Ph(2-CF₃) 34-12 Me Me H ClPh(2-F-6-Cl) 34-13 Me Me H Br Ph(2-F) 34-14 Me Me H Br Ph(2,6-F₂) 34-15Me Me H Br Ph(2-Cl) 34-16 Me Me H Br Ph(2-Me) 34-17 Me Me H Br Ph(2-CF₃)34-18 Me Me H Br Ph(2-F-6-Cl) 34-19 Me Me H Me Ph(2-F) 34-20 Me Me H MePh(2,6-F₂) 34-21 Me Me H Me Ph(2-Cl) 34-22 Me Me H Me Ph(2-Me) 34-23 MeMe H Me Ph(2-CF₃) 34-24 Me Me H Me Ph(2-F-6-Cl) 34-25 Me Me H Et Ph(2-F)34-26 Me Me H Et Ph(2,6-F₂) 34-27 Me Me H Et Ph(2-Cl) 34-28 Me Me H EtPh(2-Me) 34-29 Me Me H Et Ph(2-CF₃) 34-30 Me Me H Et Ph(2-F-6-Cl)

TABLE 35

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 35-1 Me Me H HPh(2-F) 35-2 Me Me H H Ph(2,6-F₂) 35-3 Me Me H H Ph(2-Cl) 35-4 Me Me H HPh(2-Me) 35-5 Me Me H H Ph(2-CF₃) 35-6 Me Me H H Ph(2-F-6-Cl) 35-7 Me MeH Cl Ph(2-F) 35-8 Me Me H Cl Ph(2,6-F₂) 35-9 Me Me H Cl Ph(2-Cl) 35-10Me Me H Cl Ph(2-Me) 35-11 Me Me H Cl Ph(2-CF₃) 35-12 Me Me H ClPh(2-F-6-Cl) 35-13 Me Me H Br Ph(2-F) 35-14 Me Me H Br Ph(2,6-F₂) 35-15Me Me H Br Ph(2-Cl) 35-16 Me Me H Br Ph(2-Me) 35-17 Me Me H Br Ph(2-CF₃)35-18 Me Me H Br Ph(2-F-6-Cl) 35-19 Me Me H Me Ph(2-F) 35-20 Me Me H MePh(2,6-F₂) 35-21 Me Me H Me Ph(2-Cl) 35-22 Me Me H Me Ph(2-Me) 35-23 MeMe H Me Ph(2-CF₃) 35-24 Me Me H Me Ph(2-F-6-Cl) 35-25 Me Me H Et Ph(2-F)35-26 Me Me H Et Ph(2,6-F₂) 35-27 Me Me H Et Ph(2-Cl) 35-28 Me Me H EtPh(2-Me) 35-29 Me Me H Et Ph(2-CF₃) 35-30 Me Me H Et Ph(2-F-6-Cl)

TABLE 36

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 36-1 Me Me H HPh(2-F) 36-2 Me Me H H Ph(2,6-F₂) 36-3 Me Me H H Ph(2-Cl) 36-4 Me Me H HPh(2-Me) 36-5 Me Me H H Ph(2-CF₃) 36-6 Me Me H H Ph(2-F-6-Cl) 36-7 Me MeH Cl Ph(2-F) 36-8 Me Me H Cl Ph(2,6-F₂) 36-9 Me Me H Cl Ph(2-Cl) 36-10Me Me H Cl Fh(2-Me) 36-11 Me Me H Cl Ph(2-CF₃) 36-12 Me Me H ClPh(2-F-6-Cl) 36-13 Me Me H Br Ph(2-F) 36-14 Me Me H Br Ph(2,6-F₂) 36-15Me Me H Br Ph(2-Cl) 36-16 Me Me H Br Ph(2-Me) 36-17 Me Me H Br Ph(2-CF₃)36-18 Me Me H Br Ph(2-F-6-Cl) 36-19 Me Me H Me Ph(2-F) 36-20 Me Me H MePh(2,6-F₂) 36-21 Me Me H Me Ph(2-Cl) 36-22 Me Me H Me Ph(2-Me) 36-23 MeMe H Me Ph(2-CF₃) 36-24 Me Me H Me Ph(2-F-6-Cl) 36-25 Me Me H Et Ph(2-F)36-26 Me Me H Et Ph(2,6-F₂) 36-27 Me Me H Et Ph(2-Cl) 36-28 Me Me H EtPh(2-Me) 36-29 Me Me H Et Ph(2-CF₃) 36-30 Me Me H Et Ph(2-F-6-Cl)

TABLE 37

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 37-1 Me Me H HPh(2-F) 37-2 Me Me H H Ph(2,6-F₂) 37-3 Me Me H H Ph(2-Cl) 37-4 Me Me H HPh(2-Me) 37-5 Me Me H H Ph(2-CF₃) 37-6 Me Me H H Ph(2-F-6-Cl) 37-7 Me MeH Cl Ph(2-F) 37-8 Me Me H Cl Ph(2,6-F₂) 37-9 Me Me H Cl Ph(2-Cl) 37-10Me Me H Cl Ph(2-Me) 37-11 Me Me H Cl Ph(2-CF₃) 37-12 Me Me H ClPh(2-F-6-Cl) 37-13 Me Me H Br Ph(2-F) 37-14 Me Me H Br Ph(2,6-F₂) 37-15Me Me H Br Ph(2-Cl) 37-16 Me Me H Br Ph(2-Me) 37-17 Me Me H Br Ph(2-CF₃)37-18 Me Me H Br Ph(2-F-6-Cl) 37-19 Me Me H Me Ph(2-F) 37-20 Me Me H MePh(2,6-F₂) 37-21 Me Me H Me Ph(2-Cl) 37-22 Me Me H Me Ph(2-Me) 37-23 MeMe H Me Ph(2-CF₃) 37-24 Me Me H Me Ph(2-F-6-Cl) 37-25 Me Me H Et Ph(2-F)37-26 Me Me H Et Ph(2,6-F₂) 37-27 Me Me H Et Ph(2-Cl) 37-28 Me Me H EtPh(2-Me) 37-29 Me Me H Et Ph(2-CF₃) 37-30 Me Me H Et Ph(2-F-6-Cl)

TABLE 38

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 38-1 Me Me H HPh(2-F) 38-2 Me Me H H Ph(2,6-F₂) 38-3 Me Me H H Ph(2-Cl) 38-4 Me Me H HPh(2-Me) 38-5 Me Me H H Ph(2-CF₃) 38-6 Me Me H H Ph(2-F-6-Cl) 38-7 Me MeH Cl Ph(2-F) 38-8 Me Me H Cl Ph(2,6-F₂) 38-9 Me Me H Cl Ph(2-Cl) 38-10Me Me H Cl Ph(2-Me) 38-11 Me Me H Cl Ph(2-CF₃) 38-12 Me Me H ClPh(2-F-6-Cl) 38-13 Me Me H Br Ph(2-F) 38-14 Me Me H Br Ph(2,6-F₂) 38-15Me Me H Br Ph(2-Cl) 38-16 Me Me H Br Ph(2-Me) 38-17 Me Me H Br Ph(2-CF₃)38-18 Me Me H Br Ph(2-F-6-Cl) 38-19 Me Me H Me Ph(2-F) 38-20 Me Me H MePh(2,6-F₂) 38-21 Me Me H Me Ph(2-Cl) 38-22 Me Me H Me Ph(2-Me) 38-23 MeMe H Me Ph(2-CF₃) 38-24 Me Me H Me Ph(2-F-6-Cl) 38-25 Me Me H Et Ph(2-F)38-26 Me Me H Et Ph(2,6-F₂) 38-27 Me Me H Et Ph(2-Cl) 38-28 Me Me H EtPh(2-Me) 38-29 Me Me H Et Ph(2-CF₃) 38-30 Me Me H Et Ph(2-F-6-Cl)

TABLE 39

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 39-1 Me Me H HPh(2-F) 39-2 Me Me H H Ph(2,6-F₂) 39-3 Me Me H H Ph(2-Cl) 39-4 Me Me H HPh(2-Me) 39-5 Me Me H H Ph(2-CF₃) 39-6 Me Me H H Ph(2-F-6-Cl) 39-7 Me MeH Cl Ph(2-F) 39-8 Me Me H Cl Ph(2,6-F₂) 39-9 Me Me H Cl Ph(2-Cl) 39-10Me Me H Cl Ph(2-Me) 39-11 Me Me H Cl Ph(2-CF₃) 39-12 Me Me H ClPh(2-F-6-Cl) 39-13 Me Me H Br Ph(2-F) 39-14 Me Me H Br Ph(2,6-F₂) 39-15Me Me H Br Ph(2-Cl) 39-16 Me Me H Br Ph(2-Me) 39-17 Me Me H Br Ph(2-CF₃)39-18 Me Me H Br Ph(2-F-6-Cl) 39-19 Me Me H Me Ph(2-F) 39-20 Me Me H MePh(2,6-F₂) 39-21 Me Me H Me Ph(2-Cl) 39-22 Me Me H Me Ph(2-Me) 39-23 MeMe H Me Ph(2-CF₃) 39-24 Me Me H Me Ph(2-F-6-Cl) 39-25 Me Me H Et Ph(2-F)39-26 Me Me H Et Ph(2,6-F₂) 39-27 Me Me H Et Ph(2-Cl) 39-28 Me Me H EtPh(2-Me) 39-29 Me Me H Et Ph(2-CF₃) 39-30 Me Me H Et Ph(2-F-6-Cl)

TABLE 40

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 40-1 Me Me H H HPh(2-F) 40-2 Me Me H H H Ph(2,6-F₂) 40-3 Me Me H H H Ph(2-Cl) 40-4 Me MeH H H Ph(2-Me) 40-5 Me Me H H H Ph(2-CF₃) 40-6 Me Me H H H Ph(2-F-6-Cl)40-7 Me Me H Cl H Ph(2-F) 40-8 Me Me H Cl H Ph(2,6-F₂) 40-9 Me Me H Cl HPh(2-Cl) 40-10 Me Me H Cl H Ph(2-Me) 40-11 Me Me H Cl H Ph(2-CF₃) 40-12Me Me H Cl H Ph(2-F-6-Cl) 40-13 Me Me H Me H Ph(2-F) 40-14 Me Me H Me HPh(2,6-F₂) 40-15 Me Me H Me H Ph(2-Cl) 40-16 Me Me H Me H Ph(2-Me) 40-17Me Me H Me H Ph(2-CF₃) 40-18 Me Me H Me H Ph(2-F-6-Cl) 40-19 Me Me H HCl Ph(2-F) 40-20 Me Me H H Cl Ph(2,6-F₂) 40-21 Me Me H H Cl Ph(2-Cl)40-22 Me Me H H Cl Ph(2-Me) 40-23 Me Me H H Cl Ph(2-CF₃) 40-24 Me Me H HCl Ph(2-F-6-Cl) 40-25 Me Me H H Me Ph(2-F) 40-26 Me Me H H Me Ph(2,6-F₂)40-27 Me Me H H Me Ph(2-Cl) 40-28 Me Me H H Me Ph(2-Me) 40-29 Me Me H HMe Ph(2-CF₃) 40-30 Me Me H H Me Ph(2-F-6-Cl) 40-31 Me Me H Me Me Ph(2-F)40-32 Me Me H Me Me Ph(2,6-F₂) 40-33 Me Me H Me Me Ph(2-Cl) 40-34 Me MeH Me Me Ph(2-Me) 40-35 Me Me H Me Me Ph(2-CF₃) 40-36 Me Me H Me MePh(2-F-6-Cl)

TABLE 41

Physical Compound properties No. R₁ R₂ R₃ X B (mp ° C.) 41-1 Me Me H H HPh(2-F) 41-2 Me Me H H H Ph(2,6-F₂) 41-3 Me Me H H H Ph(2-Cl) 41-4 Me MeH H H Ph(2-Me) 41-5 Me Me H H H Ph(2-CF₃) 41-6 Me Me H H H Ph(2-F-6-Cl)41-7 Me Me H Cl H Ph(2-F) 41-8 Me Me H Cl H Ph(2,6-F₂) 41-9 Me Me H Cl HPh(2-Cl) 41-10 Me Me H Cl H Ph(2-Me) 41-11 Me Me H Cl H Ph(2-CF₃) 41-12Me Me H Cl H Ph(2-F-6-Cl) 41-13 Me Me H Me H Ph(2-F) 41-14 Me Me H Me HPh(2,6-F₂) 41-15 Me Me H Me H Ph(2-Cl) 41-16 Me Me H Me H Ph(2-Me) 41-17Me Me H Me H Ph(2-CF₃) 41-18 Me Me H Me H Ph(2-F-6-Cl) 41-19 Me Me H HCl Ph(2-F) 41-20 Me Me H H Cl Ph(2,6-F₂) 41-21 Me Me H H Cl Ph(2-Cl)41-22 Me Me H H Cl Ph(2-Me) 41-23 Me Me H H Cl Ph(2-CF₃) 41-24 Me Me H HCl Ph(2-F-6-Cl) 41-25 Me Me H H Me Ph(2-F) 41-26 Me Me H H Me Ph(2,6-F₂)41-27 Me Me H H Me Ph(2-Cl) 41-28 Me Me H H Me Ph(2-Me) 41-29 Me Me H HMe Ph(2-CF₃) 41-30 Me Me H H Me Ph(2-F-6-Cl) 41-31 Me Me H Me Me Ph(2-F)41-32 Me Me H Me Me Ph(2,6-F₂) 41-33 Me Me H Me Me Ph(2-Cl) 41-34 Me MeH Me Me Ph(2-Me) 41-35 Me Me H Me Me Ph(2-CF₃) 41-36 Me Me H Me MePh(2-F-6-Cl)

TABLE 42

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ B (mp ° C.) 42-1 MeMe H H H H Ph(2-F) 42-2 Me Me H H H H Ph(2,6-F₂) 42-3 Me Me H H H HPh(2-Cl) 42-4 Me Me H H H H Ph(2-Me) 42-5 Me Me H H H H Ph(2-CF₃) 42-6Me Me H H H H Ph(2-F-6-Cl) 42-7 Me Me H H Cl H Ph(2-F) 42-8 Me Me H H ClH Ph(2,6-F₂) 42-9 Me Me H H Cl H Ph(2-Cl) 42-10 Me Me H H Cl H Ph(2-Me)42-11 Me Me H H Cl H Ph(2-CF₃) 42-12 Me Me H H Cl H Ph(2-F-6-Cl) 42-13Me Me H H Me H Ph(2-F) 42-14 Me Me H H Me H Ph(2,6-F₂) 42-15 Me Me H HMe H Ph(2-Cl) 42-16 Me Me H H Me H Ph(2-Me) 42-17 Me Me H H Me HPh(2-CF₃) 42-18 Me Me H H Me H Ph(2-F-6-Cl) 42-19 Me Me H H H Me Ph(2-F)42-20 Me Me H H H Me Ph(2,6 F₂) 42-21 Me Me H H H Me Ph(2-Cl) 42-22 MeMe H H H Me Ph(2-Me) 42-23 Me Me H H H Me Ph(2-CF₃) 42-24 Me Me H H H MePh(2-F-6-Cl) 42-25 Me Me H Me H H Ph(2-F) 42-26 Me Me H Me H HPh(2,6-F₂) 42-27 Me Me H Me H H Ph(2-Cl) 42-28 Me Me H Me H H Ph(2-Me)42-29 Me Me H Me H H Ph(2-CF₃) 42-30 Me Me H Me H H Ph(2-F-6-Cl) 42-31Me Me H Me Cl H Ph(2-F) 42-32 Me Me H Me Cl H Ph(2,6-F₂) 42-33 Me Me HMe Cl H Ph(2-Cl) 42-34 Me Me H Me Cl H Ph(2-Me) 42-35 Me Me H Me Cl HPh(2-CF₃) 42-36 Me Me H Me Cl H Ph(2-F-6-Cl) 42-37 Me Me H Me Me HPh(2-F) 42-38 Me Me H Me Me H Ph(2,6-F₂) 42-39 Me Me H Me Me H Ph(2-Cl)42-40 Me Me H Me Me H Ph(2-Me) 42-41 Me Me H Me Me H Ph(2-CF₃) 42-42 MeMe H Me Me H Ph(2-F-6-Cl) 42-43 Me Me H Me H Me Ph(2-F) 42-44 Me Me H MeH Me Ph(2,6-F₂) 42-45 Me Me H Me H Me Ph(2-Cl) 42-46 Me Me H Me H MePh(2-Me) 42-47 Me Me H Me H Me Ph(2-CF₃) 42-48 Me Me H Me H MePh(2-F-6-Cl)

TABLE 43

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ B (mp ° C.) 43-1 MeMe H H H H Ph(2-F) 43-2 Me Me H H H H Ph(2,6-F₂) 43-3 Me Me H H H HPh(2-Cl) 43-4 Me Me H H H H Ph(2-Me) 43-5 Me Me H H H H Ph(2-CF₃) 43-6Me Me H H H H Ph(2-F-6-Cl) 43-7 Me Me H H Cl H Ph(2-F) 43-8 Me Me H H ClH Ph(2,6-F₂) 43-9 Me Me H H Cl H Ph(2-Cl) 43-10 Me Me H H Cl H Ph(2-Me)43-11 Me Me H H Cl H Ph(2-CF₃) 43-12 Me Me H H Cl H Ph(2-F-6-Cl) 43-13Me Me H H Me H Ph(2-F) 43-14 Me Me H H Me H Ph(2,6-F₂) 43-15 Me Me H HMe H Ph(2-Cl) 43-16 Me Me H H Me H Ph(2-Me) 43-17 Me Me H H Me HPh(2-CF₃) 43-18 Me Me H H Me H Ph(2-F-6-Cl) 43-19 Me Me H H H Me Ph(2-F)43-20 Me Me H H H Me Ph(2,6-F₂) 43-21 Me Me H H H Me Ph(2-Cl) 43-22 MeMe H H H Me Ph(2-Me) 43-23 Me Me H H H Me Ph(2-CF₃) 43-24 Me Me H H H MePh(2-F-6-Cl) 43-25 Me Me H Me H H Ph(2-F) 43-26 Me Me H Me H HPh(2,6-F₂) 43-27 Me Me H Me H H Ph(2-Cl) 43-28 Me Me H Me H H Ph(2-Me)43-29 Me Me H Me H H Ph(2-CF₃) 43-30 Me Me H Me H H Ph(2-F-6-Cl) 43-31Me Me H Me Cl H Ph(2-F) 43-32 Me Me H Me Cl H Ph(2,6-F₂) 43-33 Me Me HMe Cl H Ph(2-Cl) 43-34 Me Me H Me Cl H Ph(2-Me) 43-35 Me Me H Me Cl HPh(2-CF₃) 43-36 Me Me H Me Cl H Ph(2-F-6-Cl) 43-37 Me Me H Me Me HPh(2-F) 43-38 Me Me H Me Me H Ph(2,6-F₂) 43-39 Me Me H Me Me H Ph(2-Cl)43-40 Me Me H Me Me H Ph(2-Me) 43-41 Me Me H Me Me H Ph(2-CF₃) 43-42 MeMe H Me Me H Ph(2-F-6-Cl) 43-43 Me Me H Me H Me Ph(2-F) 43-44 Me Me H MeH Me Ph(2,6-F₂) 43-45 Me Me H Me H Me Ph(2-Cl) 43-46 Me Me H Me H MePh(2-Me) 43-47 Me Me H Me H Me Ph(2-CF₃) 43-48 Me Me H Me H MePh(2-F-6-Cl)

TABLE 44

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ B (mp ° C.) 44-1 MeMe H H H H Ph(2-F) 44-2 Me Me H H H H Ph(2,6-F₂) 44-3 Me Me H H H HPh(2-Cl) 44-4 Me Me H H H H Ph(2-Me) 44-5 Me Me H H H H Ph(2-CF₃) 44-6Me Me H H H H Ph(2-F-6-Cl) 44-7 Me Me H H Cl H Ph(2-F) 44-8 Me Me H H ClH Ph(2,6-F₂) 44-9 Me Me H H Cl H Ph(2-Cl) 44-10 Me Me H H Cl H Ph(2-Me)44-11 Me Me H H Cl H Ph(2-CF₃) 44-12 Me Me H H Cl H Ph(2-F-6-Cl) 44-13Me Me H H Me H Ph(2-F) 44-14 Me Me H H Me H Ph(2,6-F₂) 44-15 Me Me H HMe H Ph(2-Cl) 44-16 Me Me H H Me H Ph(2-Me) 44-17 Me Me H H Me HPh(2-CF₃) 44-18 Me Me H H Me H Ph(2-F-6-Cl) 44-19 Me Me H H H Me Ph(2-F)44-20 Me Me H H H Me Ph(2,6-F₂) 44-21 Me Me H H H Me Ph(2-Cl) 44-22 MeMe H H H Me Ph(2-Me) 44-23 Me Me H H H Me Ph(2-CF₃) 44-24 Me Me H H H MePh(2-F-6-Cl) 44-25 Me Me H Me H H Ph(2-F) 44-26 Me Me H Me H HPh(2,6-F₂) 44-27 Me Me H Me H H Ph(2-Cl) 44-28 Me Me H Me H H Ph(2-Me)44-29 Me Me H Me H H Ph(2-CF₃) 44-30 Me Me H Me H H Ph(2-F-6-Cl) 44-31Me Me H Me Cl H Ph(2-F) 44-32 Me Me H Me Cl H Ph(2,6-F₂) 44-33 Me Me HMe Cl H Ph(2-Cl) 44-34 Me Me H Me Cl H Ph(2-Me) 44-35 Me Me H Me Cl HPh(2-CF₂) 44-36 Me Me H Me Cl H Ph(2-F-6-Cl) 44-37 Me Me H Me Me HPh(2-F) 44-38 Me Me H Me Me H Ph(2,6-F₂) 44-39 Me Me H Me Me H Ph(2-Cl)44-40 Me Me H Me Me H Ph(2-Me) 44-41 Me Me H Me Me H Ph(2-CF₃) 44-42 MeMe H Me Me H Ph(2-F-6-Cl) 44-43 Me Me H Me H Me Ph(2-F) 44-44 Me Me H MeH Me Ph(2,6-F₂) 44-45 Me Me H Me H Me Ph(2-Cl) 44-46 Me Me H Me H MePh(2-Me) 44-47 Me Me H Me H Me Ph(2-CF₃) 44-48 Me Me H Me H MePh(2-F-6-Cl)

TABLE 45

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 45-1 Me Me HH H Ph(2-F) 45-2 Me Me H H H Ph(2,6-F₂) 45-3 Me Me H H H Ph(2-Cl) 45-4Me Me H H H Ph(2-Me) 45-5 Me Me H H H Ph(2-CF₃) 45-6 Me Me H H HPh(2-F-6-Cl) 45-7 Me Me H Cl H Ph(2-F) 45-8 Me Me H Cl H Ph(2,6-F₂) 45-9Me Me H Cl H Ph(2-Cl) 45-10 Me Me H Cl H Ph(2-Me) 45-11 Me Me H Cl HPh(2-CF₃) 45-12 Me Me H Cl H Ph(2-F-6-Cl) 45-13 Me Me H Me H Ph(2-F)45-14 Me Me H Me H Ph(2,6-F₂) 45-15 Me Me H Me H Ph(2-Cl) 45-16 Me Me HMe H Ph(2-Me) 45-17 Me Me H Me H Ph(2-CF₃) 45-18 Me Me H Me HPh(2-F-6-Cl) 45-19 Me Me H H Cl Ph(2-F) 45-20 Me Me H H Cl Ph(2,6-F₂)45-21 Me Me H H Cl Ph(2-Cl) 45-22 Me Me H H Cl Ph(2-Me) 45-23 Me Me H HCl Ph(2-CF₃) 45-24 Me Me H H Cl Ph(2-F-6-Cl) 45-25 Me Me H H Me Ph(2-F)45-26 Me Me H H Me Ph(2,6-F₂) 45-27 Me Me H H Me Ph(2-Cl) 45-28 Me Me HH Me Ph(2-Me) 45-29 Me Me H H Me Ph(2-CF₃) 45-30 Me Me H H MePh(2-F-6-Cl) 45-31 Me Me H Me Me Ph(2-F) 45-32 Me Me H Me Me Ph(2,6-F₂)45-33 Me Me H Me Me Ph(2-Cl) 45-34 Me Me H Me Me Ph(2-Me) 45-35 Me Me HMe Me Ph(2-CF₃) 45-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 46

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ B (mp ° C.) 46-1 MeMe H H H H Ph(2-F) 46-2 Me Me H H H H Ph(2,6-F₂) 46-3 Me Me H H H HPh(2-Cl) 46-4 Me Me H H H H Ph(2-Me) 46-5 Me Me H H H H Ph(2-CF₃) 46-6Me Me H H H H Ph(2-F-6-Cl) 46-7 Me Me H H Cl H Ph(2-F) 46-8 Me Me H H ClH Ph(2,6-F₂) 46-9 Me Me H H Cl H Ph(2-Cl) 46-10 Me Me H H Cl H Ph(2-Me)46-11 Me Me H H Cl H Ph(2-CF₃) 46-12 Me Me H H Cl H Ph(2-F-6-Cl) 46-13Me Me H H Me H Ph(2-F) 46-14 Me Me H H Me H Ph(2,6-F₂) 46-15 Me Me H HMe H Ph(2-Cl) 46-16 Me Me H H Me H Ph(2-Me) 46-17 Me Me H H Me HPh(2-CF₃) 46-18 Me Me H H Me H Ph(2-F-6-Cl) 46-19 Me Me H H H Me Ph(2-F)46-20 Me Me H H H Me Ph(2,6-F₂) 46-21 Me Me H H H Me Ph(2-Cl) 46-22 MeMe H H H Me Ph(2-Me) 46-23 Me Me H H H Me Ph(2-CF₃) 46-24 Me Me H H H MePh(2-F-6-Cl) 46-25 Me Me H Me H H Ph(2-F) 46-26 Me Me H Me H HPh(2,6-F₂) 46-27 Me Me H Me H H Ph(2-Cl) 46-28 Me Me H Me H H Ph(2-Me)46-29 Me Me H Me H H Ph(2-CF₃) 46-30 Me Me H Me H H Ph(2-F-6-Cl) 46-31Me Me H Me Cl H Ph(2-F) 46-32 Me Me H Me Cl H Ph(2,6-F₂) 46-33 Me Me HMe Cl H Ph(2-Cl) 46-34 Me Me H Me Cl H Ph(2-Me) 46-35 Me Me H Me Cl HPh(2-CF₃) 46-36 Me Me H Me Cl H Ph(2-F-6-Cl) 46-37 Me Me H Me Me HPh(2-F) 46-38 Me Me H Me Me H Ph(2,6-F₂) 46-39 Me Me H Me Me H Ph(2-Cl)46-40 Me Me H Me Me H Ph(2-Me) 46-41 Me Me H Me Me H Ph(2-CF₃) 46-42 MeMe H Me Me H Ph(2-F-6-Cl) 46-43 Me Me H Me H Me Ph(2-F) 46-44 Me Me H MeH Me Ph(2,6-F₂) 46-45 Me Me H Me H Me Ph(2-Cl) 46-46 Me Me H Me H MePh(2-Me) 46-47 Me Me H Me H Me Ph(2-CF₃) 46-48 Me Me H Me H MePh(2-F-6-Cl)

TABLE 47

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 47-1 Me Me HH H Ph(2-F) 47-2 Me Me H H H Ph(2,6-F₂) 47-3 Me Me H H H Ph(2-Cl) 47-4Me Me H H H Ph(2-Me) 47-5 Me Me H H H Ph(2-CF₃) 47-6 Me Me H H HPh(2-F-6-Cl) 47-7 Me Me H Cl H Ph(2-F) 47-8 Me Me H Cl H Ph(2,6-F₂) 47-9Me Me H Cl H Ph(2-Cl) 47-10 Me Me H Cl H Ph(2-Me) 47-11 Me Me H Cl HPh(2-CF₃) 47-12 Me Me H Cl H Ph(2-F-6-Cl) 47-13 Me Me H Me H Ph(2-F)47-14 Me Me H Me H Ph(2,6-F₂) 47-15 Me Me H Me H Ph(2-Cl) 47-16 Me Me HMe H Ph(2-Me) 47-17 Me Me H Me H Ph(2-CF₃) 47-18 Me Me H Me HPh(2-F-6-Cl) 47-19 Me Me H H Cl Ph(2-F) 47-20 Me Me H H Cl Ph(2,6-F₂)47-21 Me Me H H Cl Ph(2-Cl) 47-22 Me Me H H Cl Ph(2-Me) 47-23 Me Me H HCl Ph(2-CF₃) 47-24 Me Me H H Cl Ph(2-F-6-Cl) 47-25 Me Me H H Me Ph(2-F)47-26 Me Me H H Me Ph(2,6-F₂) 47-27 Me Me H H Me Ph(2-Cl) 47-28 Me Me HH Me Ph(2-Me) 47-29 Me Me H H Me Ph(2-CF₃) 47-30 Me Me H H MePh(2-F-6-Cl) 47-31 Me Me H Me Me Ph(2-F) 47-32 Me Me H Me Me Ph(2,6-F₂)47-33 Me Me H Me Me Ph(2-Cl) 47-34 Me Me H Me Me Ph(2-Me) 47-35 Me Me HMe Me Ph(2-CF₃) 47-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 48

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 48-1 Me Me HH H Ph(2-F) 48-2 Me Me H H H Ph(2,6-F₂) 48-3 Me Me H H H Ph(2-Cl) 48-4Me Me H H H Ph(2-Me) 48-5 Me Me H H H Ph(2-CF₃) 48-6 Me Me H H HPh(2-F-6-Cl) 48-7 Me Me H Cl H Ph(2-F) 48-8 Me Me H Cl H Ph(2,6-F₂) 48-9Me Me H Cl H Ph(2-Cl) 48-10 Me Me H Cl H Ph(2-Me) 48-11 Me Me H Cl HPh(2-CF₃) 48-12 Me Me H Cl H Ph(2-F-6-Cl) 48-13 Me Me H Me H Ph(2-F)48-14 Me Me H Me H Ph(2,6-F₂) 48-15 Me Me H Me H Ph(2-Cl) 48-16 Me Me HMe H Ph(2-Me) 48-17 Me Me H Me H Ph(2-CF₃) 48-18 Me Me H Me HPh(2-F-6-Cl) 48-19 Me Me H H Cl Ph(2-F) 48-20 Me Me H H Cl Ph(2,6-F₂)48-21 Me Me H H Cl Ph(2-Cl) 48-22 Me Me H H Cl Ph(2-Me) 48-23 Me Me H HCl Ph(2-CF₃) 48-24 Me Me H H Cl Ph(2-F-6-Cl) 48-25 Me Me H H Me Ph(2-F)48-26 Me Me H H Me Ph(2,6-F₂) 48-27 Me Me H H Me Ph(2-Cl) 48-28 Me Me HH Me Ph(2-Me) 48-29 Me Me H H Me Ph(2-CF₃) 48-30 Me Me H H MePh(2-F-6-Cl) 48-31 Me Me H Me Me Ph(2-F) 48-32 Me Me H Me Me Ph(2,6-F₂)48-33 Me Me H Me Me Ph(2-Cl) 48-34 Me Me H Me Me Ph(2-Me) 48-35 Me Me HMe Me Ph(2-CF₃) 48-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 49

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 49-1 Me Me HH H Ph(2-F) 49-2 Me Me H H H Ph(2,6-F₂) 49-3 Me Me H H H Ph(2-Cl) 49-4Me Me H H H Ph(2-Me) 49-5 Me Me H H H Ph(2-CF₃) 49-6 Me Me H H HPh(2-F-6-Cl) 49-7 Me Me H Cl H Ph(2-F) 49-8 Me Me H Cl H Ph(2,6-F₂) 49-9Me Me H Cl H Ph(2-Cl) 49-10 Me Me H Cl H Ph(2-Me) 49-11 Me Me H Cl HPh(2-CF₃) 49-12 Me Me H Cl H Ph(2-F-6-Cl) 49-13 Me Me H Me H Ph(2-F)49-14 Me Me H Me H Ph(2,6-F₂) 49-15 Me Me H Me H Ph(2-Cl) 49-16 Me Me HMe H Ph(2-Me) 49-17 Me Me H Me H Ph(2-CF₃) 49-18 Me Me H Me HPh(2-F-6-Cl) 49-19 Me Me H H Ci Ph(2-F) 49-20 Me Me H H Cl Ph(2,6-F₂)49-21 Me Me H H Cl Ph(2-Cl) 49-22 Me Me H H Cl Ph(2-Me) 49-23 Me Me H HCl Ph(2-CF₃) 49-24 Me Me H H Cl Ph(2-F-6-Cl) 49-25 Me Me H H Me Ph(2-F)49-26 Me Me H H Me Ph(2,6-F₂) 49-27 Me Me H H Me Ph(2-Cl) 49-28 Me Me HH Me Ph(2-Me) 49-29 Me Me H H Me Ph(2-CF₃) 49-30 Me Me H H MePh(2-F-6-Cl) 49-31 Me Me H Me Me Ph(2-F) 49-32 Me Me H Me Me Ph(2,6-F₂)49-33 Me Me H Me Me Ph(2-Cl) 49-34 Me Me H Me Me Ph(2-Me) 49-35 Me Me HMe Me Ph(2-CF₃) 49-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 50

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 50-1 Me Me HH H Ph(2-F) 50-2 Me Me H H H Ph(2,6-F₂) 50-3 Me Me H H H Ph(2-Cl) 50-4Me Me H H H Ph(2-Me) 50-5 Me Me H H H Ph(2-CF₃) 50-6 Me Me H H HPh(2-F-6-Cl) 50-7 Me Me H Cl H Ph(2-F) 50-8 Me Me H Cl H Ph(2,6-F₂) 50-9Me Me H Cl H Ph(2-Cl) 50-10 Me Me H Cl H Ph(2-Me) 50-11 Me Me H Cl HPh(2-CF₃) 50-12 Me Me H Cl H Ph(2-F-6-Cl) 50-13 Me Me H Me H Ph(2-F)50-14 Me Me H Me H Ph(2,6-F₂) 50-15 Me Me H Me H Ph(2-Cl) 50-16 Me Me HMe H Ph(2-Me) 50-17 Me Me H Me H Ph(2-CF₃) 50-18 Me Me H Me HPh(2-F-6-Cl) 50-19 Me Me H H Cl Ph(2-F) 50-20 Me Me H H Cl Ph(2,6-F₂)50-21 Me Me H H Cl Ph(2-Cl) 50-22 Me Me H H Cl Ph(2-Me) 50-23 Me Me H HCl Ph(2-CF₃) 50-24 Me Me H H Cl Ph(2-F-6-Cl) 50-25 Me Me H H Me Ph(2-F)50-26 Me Me H H Me Ph(2,6-F₂) 50-27 Me Me H H Me Ph(2-Cl) 50-28 Me Me HH Me Ph(2-Me) 50-29 Me Me H H Me Ph(2-CF₃) 50-30 Me Me H H MePh(2-F-6-Cl) 50-31 Me Me H Me Me Ph(2-F) 50-32 Me Me H Me Me Ph(2,6-F₂)50-33 Me Me H Me Me Ph(2-Cl) 50-34 Me Me H Me Me Ph(2-Me) 50-35 Me Me HMe Me Ph(2-CF₃) 50-36 Me Me H Me Me Ph(2-F-6-Cl)

TABLE 51

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 51-1 Me Me HH H Ph(2-F) 121-122 51-2 Me Me H H H Ph(2,6-F₂) 147-148 51-3 Me Me H H HPh(2-Cl) 51-4 Me Me H H H Ph(2-Me) 51-5 Me Me H H H Ph(2-CF₃) 51-6 Me MeH H H Ph(2-F-6-Cl) 51-7 Me Me H Me H Ph(2-F) 51-8 Me Me H Me HPh(2,6-F₂) 51-9 Me Me H Me H Ph(2-Cl) 51-10 Me Me H Me H Ph(2-Me) 51-11Me Me H Me H Ph(2-CF₃) 51-12 Me Me H Me H Ph(2-F-6-Cl) 51-13 Me Me H MeMe Ph(2-F) 51-14 Me Me H Me Me Ph(2,6-F₂) 51-15 Me Me H Me Me Ph(2-Cl)51-16 Me Me H Me Me Ph(2-Me) 51-17 Me Me H Me Me Ph(2-CF₃) 51-18 Me Me HMe Me Ph(2-F-6-Cl) 51-19 Me Me H Me Cl Ph(2-F) 51-20 Me Me H Me ClPh(2,6-F₂) 51-21 Me Me H Me Cl Ph(2-Cl) 51-22 Me Me H Me Cl Ph(2-Me)51-23 Me Me H Me Cl Ph(2-CF₃) 51-24 Me Me H Me Cl Ph(2-F-6-Cl) 51-25 MeMe H Me Br Ph(2-F) 51-26 Me Me H Me Br Ph(2,6-F₂) 51-27 Me Me H Me BrPh(2-Cl) 51-28 Me Me H Me Br Ph(2-Me) 51-29 Me Me H Me Br Ph(2-CF₃)51-30 Me Me H Me Br Ph(2-F-6-Cl) 51-31 Me Me H Me CF₃ Ph(2-F) 51-32 MeMe H Me CF₃ Ph(2,6-F₂) 51-33 Me Me H Me CF₃ Ph(2-Cl) 51-34 Me Me H MeCF₃ Ph(2-Me) 51-35 Me Me H Me CF₃ Ph(2-CF₃) 51-36 Me Me H Me CF₃Ph(2-F-6-Cl) 51-37 Me Me H Me OCF₃ Ph(2-F) 51-38 Me Me H Me OCF₃Ph(2,6-F₂) 51-39 Me Me H Me OCF₃ Ph(2-Cl) 51-40 Me Me H Me OCF₃ Ph(2-Me)51-41 Me Me H Me OCF₃ Ph(2-CF₃) 51-42 Me Me H Me OCF₃ Ph(2-F-6-Cl) 51-43Me Me H Me OCHF₂ Ph(2-F) 51-44 Me Me H Me OCHF₂ Ph(2,6-F₂) 51-45 Me Me HMe OCHF₂ Ph(2-Cl) 51-46 Me Me H Me OCHF₂ Ph(2-Me) 51-47 Me Me H Me OCHF₂Ph(2-CF₃) 51-48 Me Me H Me OCHF₂ Ph(2-F-6-Cl) 51-49 Me Me H Me OCH₂CF₃Ph(2-F) 51-50 Me Me H Me OCH₂CF₃ Ph(2,6-F₂) 51-51 Me Me H Me OCH₂CF₃Ph(2-Cl) 51-53 Me Me H Me OCH₂CF₃ Ph(2-CF₃) 51-54 Me Me H Me OCH₂CF₃Ph(2-F-6-Cl) 51-55 Me Me H Cl H Ph(2-F) 51-56 Me Me H Cl H Ph(2,6-F₂)51-57 Me Me H Cl H Ph(2-Cl) 51-58 Me Me H Cl H Ph(2-Me) 51-59 Me Me H ClH Ph(2-CF₃) 51-60 Me Me H Cl H Ph(2-F-6-Cl) 51-61 Me Me H Cl Me Ph(2-F)51-62 Me Me H Cl Me Ph(2,6-F₂) 51-63 Me Me H Cl Me Ph(2-Cl) 51-64 Me MeH Cl Me Ph(2-Me) 51-65 Me Me H Cl Me Ph(2-CF₃) 51-66 Me Me H Cl MePh(2-F-6-Cl) 51-67 Me Me H Cl Cl Ph(2-F) 51-68 Me Me H Cl Cl Ph(2,6-F₂)51-69 Me Me H Cl Cl Ph(2-Cl) 51-70 Me Me H Cl Cl Ph(2-Me) 51-71 Me Me HCl Cl Ph(2-CF₃) 51-72 Me Me H Cl Cl Ph(2-F-6-Cl) 51-73 Me Me H Cl BrPh(2-F) 51-74 Me Me H Cl Br Ph(2,6-F₂) 51-75 Me Me H Cl Br Ph(2-Cl)51-76 Me Me H Cl Br Ph(2-Me) 51-77 Me Me H Cl Br Ph(2-CF₃) 51-78 Me Me HCl Br Ph(2-F-6-Cl) 51-79 Me Me H Cl CF₃ Ph(2-F) 51-80 Me Me H Cl CF₃Ph(2,6-F₂) 51-81 Me Me H Cl CF₃ Ph(2-Cl) 51-82 Me Me H Cl CF₃ Ph(2-Me)51-83 Me Me H Cl CF₃ Ph(2-CF₃) 51-84 Me Me H Cl CF₃ Ph(2-F-6-Cl) 51-85Me Me H Cl OCF₃ Ph(2-F) 51-86 Me Me H Cl OCF₃ Ph(2,6-F₂) 51-87 Me Me HCl OCF₃ Ph(2-Cl) 51-88 Me Me H Cl OCF₃ Ph(2-Me) 51-89 Me Me H Cl OCF₃Ph(2-CF₃) 51-90 Me Me H Cl OCF₃ Ph(2-F-6-Cl) 51-91 Me Me H Cl OCHF₂Ph(2-F) 51-92 Me Me H Cl OCHF₂ Ph(2,6-F₂) 51-93 Me Me H Cl OCHF₂Ph(2-Cl) 51-94 Me Me H Cl OCHF₂ Ph(2-Me) 51-95 Me Me H Cl OCHF₂Ph(2-CF₃) 51-96 Me Me H Cl OCHF₂ Ph(2-F-6-Cl) 51-97 Me Me H Cl OCH₂CF₃Ph(2-F) 51-98 Me Me H Cl OCH₂CF₃ Ph(2,6-F₂) 51-99 Me Me H Cl OCH₂CF₃Ph(2-Cl) 51-100 Me Me H Cl OCH₂CF₃ Ph(2-Me) 51-101 Me Me H Cl OCH₂CF₃Ph(2-CF₃) 51-102 Me Me H Cl OCH₂CF₃ Ph(2-F-6-Cl)

TABLE 52

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ X₃ B (mp ° C.) 52-1 MeMe H H H H Ph(2-F) 52-2 Me Me H H H H Ph(2,6-F₂) 52-3 Me Me H H H HPh(2-Cl) 52-4 Me Me H H H H Ph(2-Me) 52-5 Me Me H H H H Ph(2-CF₃) 52-6Me Me H H H H Ph(2-F-6-Cl) 52-7 Me Me H H Me H Ph(2-F) 52-8 Me Me H H MeH Ph(2,6-F₂) 52-9 Me Me H H Me H Ph(2-Cl) 52-10 Me Me H H Me H Ph(2-Me)52-11 Me Me H H Me H Ph(2-CF₃) 52-12 Me Me H H Me H Ph(2-F-6-Cl) 52-13Me Me H H H Me Ph(2-F) 52-14 Me Me H H H Me Ph(2,6-F₂) 52-15 Me Me H H HMe Ph(2-Cl) 52-16 Me Me H H H Me Ph(2-Me) 52-17 Me Me H H H Me Ph(2-CF₃)52-18 Me Me H H H Me Ph(2-F-6-Cl) 52-19 Me Me H F H H Ph(2-F) 52-20 MeMe H F H H Ph(2,6-F₂) 52-21 Me Me H F H H Ph(2-Cl) 52-22 Me Me H F H HPh(2-Me) 52-23 Me Me H F H H Ph(2-CF₃) 52-24 Me Me H F H H Ph(2-F-6-Cl)52-25 Me Me H F Me H Ph(2-F) 52-26 Me Me H F Me H Ph(2,6-F₂) 52-27 Me MeH F Me H Ph(2-Cl) 52-28 Me Me H F Me H Ph(2-Me) 52-29 Me Me H F Me HPh(2-CF₃) 52-30 Me Me H F Me H Ph(2-F-6-Cl) 52-31 Me Me H F Cl H Ph(2-F)52-32 Me Me H F Cl H Ph(2,6-F₂) 52-33 Me Me H F Cl H Ph(2-Cl) 52-34 MeMe H F Cl H Ph(2-Me) 52-35 Me Me H F Cl H Ph(2-CF₃) 52-36 Me Me H F Cl HPh(2-F-6-Cl) 52-37 Me Me H F H Me Ph(2-F) 52-38 Me Me H F H MePh(2,6-F₂) 52-39 Me Me H F H Me Ph(2-Cl) 52-40 Me Me H F H Me Ph(2-Me)52-41 Me Me H F H Me Ph(2-CF₃) 52-42 Me Me H F H Me Ph(2-F-6-Cl) 52-43Me Me H H Cl H Ph(2-F) 52-44 Me Me H H Cl H Ph(2,6-F₂) 52-45 Me Me H HCl H Ph(2-Cl) 52-46 Me Me H H Cl H Ph(2-Me) 52-47 Me Me H H Cl HPh(2-CF₃) 52-48 Me Me H H Cl H Ph(2-F-6-Cl) 52-49 Me Me H H H Cl Ph(2-F)52-50 Me Me H H H Cl Ph(2,6-F₂) 52-51 Me Me H H H Cl Ph(2-Cl) 52-52 MeMe H H H Cl Ph(2-Me) 52-53 Me Me H H H Cl Ph(2-CF₃) 52-54 Me Me H H H ClPh(2-F-6-Cl) 52-55 Me Me H F H Cl Ph(2-F) 52-56 Me Me H F H ClPh(2,6-F₂) 52-57 Me Me H F H Cl Ph(2-Cl) 52-58 Me Me H F H Cl Ph(2-Me)52-59 Me Me H F H Cl Ph(2-CF₃) 52-60 Me Me H F H Cl Ph(2-F-6-Cl)

TABLE 53

Physical Compound properties No. R₁ R₂ R₃ X₁ X₂ B (mp ° C.) 53-1 Me Me HH H Ph(2-F) 53-2 Me Me H H H Ph(2,6-F₂) 53-3 Me Me H H H Ph(2-Cl) 53-4Me Me H H H Ph(2-Me) 53-5 Me Me H H H Ph(2-CF₃) 53-6 Me Me H H HPh(2-F-6-Cl) 53-7 Me Me H Cl H Ph(2-F) 53-8 Me Me H Cl H Ph(2,6-F₂) 53-9Me Me H Cl H Ph(2-Cl) 53-10 Me Me H Cl H Ph(2-Me) 53-11 Me Me H Cl HPh(2-CF₃) 53-12 Me Me H Cl H Ph(2-F-6-Cl) 53-13 Me Me H Me H Ph(2-F)53-14 Me Me H Me H Ph(2,6-F₂) 53-15 Me Me H Me H Ph(2-Cl) 53-16 Me Me HMe H Ph(2-Me) 53-17 Me Me H Me H Ph(2-CF₃) 53-18 Me Me H Me HPh(2-F-6-Cl) 53-19 Me Me H H Cl Ph(2-F) 53-20 Me Me H H Cl Ph(2,6-F₂)53-21 Me Me H H Cl Ph(2-Cl) 53-22 Me Me H H Cl Ph(2-Me) 53-23 Me Me H HCl Ph(2-CF₃) 53-24 Me Me H H Cl Ph(2-F-6-Cl) 53-25 Me Me H H Me Ph(2-F)53-26 Me Me H H Me Ph(2,6-F₂) 53-27 Me Me H H Me Ph(2-Cl) 53-28 Me Me HH Me Ph(2-Me) 53-29 Me Me H H Me Ph(2-CF₃) 53-30 Me Me H H MePh(2-F-6-Cl) 53-31 Me Me H Me Me Ph(2-F) 53-32 Me Me H Me Me Ph(2,6-F₂)53-33 Me Me H Me Me Ph(2-Cl) 53-34 Me Me H Me Me Ph(2-Me) 53-35 Me Me HMe Me Ph(2-CF₃) 53-36 Me Me H Me Me Ph(2-F-6-Cl)

Now, Test Examples will be described.

TEST EXAMPLE 1 Test on Southern Root-knot Nematode (Meloidgyneincognita) (Soil incorporation)

To 300 ml of the soil contaminated by southern root-knot nematode, 7 mlof a chemical solution having the concentration of the compound of thepresent invention adjusted to be 1600 ppm, is poured, followed by mixingso that the compound is uniformly dispersed. The treated soil is putinto a pot (diameter: 9 cm, height: 8 cm), and then a tomato seedling in2-leaf stage is transplanted and placed in a greenhouse. After three tofour weeks from the transplantation of the tomato, the root knot indexis determined based on the following standards. The compound of thepresent invention shows high controlling effects at a level of a rootknot index of not more than 1. For example, the compound Nos. 1-25,1-26, 1-73, 1-100, 1-122, 1-123, 1-125, 1-127, 1-130, 1-131, 1-133,1-136, 1-137, 1-139, 1-140, 1-172, 1-173, 1-177, 5-5, 5-9, 5-11, 5-16,5-20, 8-2, 8-5, 13-2, 13-4, 13-6, 13-7, 13-18, 13-19, 13-44, 13-45,16-32, 16-37 and 16-38 were at a level of a root knot index of not morethan 1.

Degree of formation of root Root knot index knots 0 No knot was formed 1Knots were formed to a slight degree 2 Knots were formed to a moderatedegree 3 Knots were formed to a heavy degree 4 Knots were formed to theheaviest degree

TEST EXAMPLE 2 Test on Cobb Root-lesion Nematode (Pratylenchuspenetrans) (Soil incorporation)

To 300 ml of the soil contaminated by Cobb root-lesion nematode, 7 ml ofa chemical solution having the concentration of the compound of thepresent invention adjusted to be 1600 ppm, is poured, followed by mixingso that the compound is uniformly dispersed. The treated soil is putinto a pot (diameter: 9 cm, height: 8 cm), and then 10 seeds of burdockare disseminated and placed in a greenhouse. After about two months fromthe dissemination of the burdock seeds, injury level of the roots isdetermined based on the following standards. The compound of the presentinvention shows high controlling effects at a level of an injury indexof not more than 1. For example, the compound Nos. 13-19 and 13-45 wereat a level of an injury index of not more than 1.

Injury index Injury level of roots 0 No injury 1 Slight injury 2Moderate injury 3 Heavy injury 4 Heaviest injury

TEST EXAMPLE 3 Test on Cobb Root-lesion Nematode (Immersion Treatment)

To a test tube made of glass (DISPOSABLE CULTURE TUBE manufactured byIWAKI Co., Ltd: internal diameter: 10 mm, lengh: 75 mm), 1 ml of achemical solution having the concentration of the compound of thepresent invention adjusted to be 40 ppm, is poured. 1 ml of water havingabout 100 of Cobb root-lesion nematodes is added thereto, followed bystirring gently. The final concentration of the compound of the presentinvention in the obtained solution is 20 ppm. Then, the top of the testtube is covered with a Para film (Manufactured by American National CanCo., Ltd) to obdurate, and then it is left at 25° C. After two days, theabove solution is transferred to a slide glass (MICRO SLIDE GLASSmanufactured by MATSUNAMI Co., Ltd: With plankton lattice lines), thenumber of inactive nematodes (including ones which do not move at least10 seconds) and the number of active nematodes are counted by amicroscope. The motility inhibition ratio (%) is calculated based on thefollowing formula. As a result, the compound of the present inventionshows high controlling effects at a level of a motility inhibition ratio(%) of not less than 70%. For example, the motility inhibition ratio ofthe compounds Nos. 13-45, 16-37 and 16-38 showed at a level of amotility inhibition ratio of not less than 70%.

Motility inhibition ratio (%)=The number of inactive nematodes/(Thenumber of active nematodes+The number of inactive nematodes)×100

TEST EXAMPLE 4 Test on Coccidia

Eimeria tenella of wild type is infected to chicks to obtain freshimmature oocysts, which are then exposed to a solution having apredetermined concentration of the compound of the present invention for10 or 30 minutes. The exposed immature oocysts are subjected tocentrifugal separation, and after removing the supernatant, a 2%potassium bichromate aqueous solution is added, followed by sporulationat 25° C. for 4 days, whereby good oosyst controlling effects areconfirmed.

TEST EXAMPLE 5 Test on Gog Filarioidea

To a dog subcutaneously infected with dog filarioidea (Dirofilariaimmitis), the compound of the present invention is orally administered.At the time of an autopsy after 200 days from the infection, the numberof adults of dog filarioidea parasitic to the lung or heart of thetreated animal is investigated, whereby good effects for controlling dogfilarioidea is confirmed.

Now, formulation Examples will be described.

FORMULATION EXAMPLE 1 (1) Compound of the present invention 20 parts byweight (2) Clay 72 parts by weight (3) Sodium lignin sulfonate  8 partsby weight

The above components are uniformly mixed to obtain a wettable powder.

FORMULATION EXAMPLE 2 (1) Compound of the present invention  5 parts byweight (2) Talc 95 parts by weight

The above components are uniformly mixed to obtain a dust.

FORMULATION EXAMPLE 3 (1) Compound of the present invention 20 parts byweight (2) N,N′-dimethylacetamide 20 parts by weight (3)Polyoxyethylenealkylphenyl ether 10 parts by weight (4) Xylene 50 partsby weight

The above components are uniformly mixed and dissolved to obtain anemulsifiable concentrate.

FORMULATION EXAMPLE 4 (1) Clay 68 parts by weight (2) Sodium ligninsulfonate  2 parts by weight (3) Polyoxyethylenealkylaryl sulfate  5parts by weight (4) Fine silica powder 25 parts by weight

A mixture of the above components is mixed with compound of the presentinvention in a weight ratio of 4:1 to obtain a wettable powder.

FORMULATION EXAMPLE 5 (1) Compound of the present invention   50 partsby weight (2) Oxylated polyalkylphenyl   2 parts by weight  phosphate-triethanolamine (3) Silicone  0.2 part by weight (4) Water47.8 parts by weight The above components are uniformly mixed andpulverized to obtain a base liquid, and (5) Sodium polycarboxylate   5parts by weight (6) Anhydrous sodium sulfate 42.8 parts by weight areadded, and the mixture is uniformly mixed and dried to obtainwater-dispersible granules.

FORMULATION EXAMPLE 6 (1) Compound of the present invention   5 parts byweight (2) Polyoxyethyleneoctylphenyl ether   1 part by weight (3)polyoxyethylene phosphoric acid ester  0.1 part by weight (4) Granularcalcium carbonate 93.9 parts by weight

The above components (1) to (3) are preliminarily uniformly mixed anddiluted with a proper amount of acetone, and then the mixture is sprayedonto the component (4), and acetone is removed to obtain granules.

FORMULATION EXAMPLE 7 (1) Compound of the present invention  2.5 partsby weight (2) N-methyl-2-pyrrolidone  2.5 parts by weight (3) Soybeanoil 95.0 parts by weight

The above components are uniformly mixed and dissolved to obtain anultra low volume formulation.

1. An acid amide derivative of the formula (I) or a salt thereof:

wherein A is phenyl which may be substituted by X, B is a heterocyclicgroup which may be substituted by Y, or a fused heterocyclic group whichmay be substituted by Y, X is halogen, alkyl, haloalkyl, alkenyl,haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkoxyalkoxy,haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkenyloxy,haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio,alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio,alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted byY, phenoxy which may be substituted by Y, benzyloxy which may besubstituted by Y, pyridyloxy which may be substituted by Y, —OR₄, —SR₅,—NR₆R₇, —CO₂R₈, —C(═O)NR₉R₁₀ or an unsaturated heterocyclic group (theunsaturated heterocyclic ring may be substituted by halogen, alkyl,haloalkyl, alkoxy or haloalkoxy), Y is halogen, alkyl, haloalkyl,alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl,haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, —ORhd 4, —CO₂R₁₁, —CONR₁₂R₁₃ or anunsaturated heterocyclic group (the unsaturated heterocyclic ring may besubstituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each ofR₁ and R₂ is alkyl, cyano or —CO₂R₁₄, or R₁ and R₂ may together form a3- to 6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl, —CO₂R₁₅, S(O)_(m)R₁₆ or —S(O)_(n)NR₁₇R₁₈,each of R₄ and R₆ is hydrogen, —C(═W)R₁₉, —C(═W)OR₂₀, —C(═W)SR₂₁,—C(═W)NR₂₂R₂₃, —S(O)_(q)R₂₄ or —S(O)rNR₂₅R₂₆, R₅ is hydrogen, —C(═W)R₁₉,—C(═W)OR₂₀, —C(═W)SR₂₁ or —C(═W)NR₂₂R₂₃, R₇ is hydrogen, alkyl orhaloalkyl, each of R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃ and R₁₄ is hydrogen oralkyl, R₁₅ is hydrogen, alkyl or alkoxy, each of R₁₆, R₁₇, R₁₈, R₁₉,R₂₀, R₂₁, R₂₂, R₂₃, R₂₄, R₂₅ and R₂₆ is alkyl, haloalkyl or phenyl,wherein the phenyl which may be substituted by halogen, alkyl,haloalkyl, alkoxy or haloalkoxy, each of m, n, q and r is from 0 to2,and W is oxygen or sulfur, provided that following is excluded: A isphenyl which may be substituted by X₁ B is pyridyl which may besubstituted by Y₁ or pyrazolyl which may be substituted by Y₁, each ofR₁ and R₂ is alkyl, or R₁ and R₂ together form a 3- to 6-memberedsaturated carbocyclic ring, R₃ is hydrogen, alkyl, alkoxyalkyl,alkylthioalkyl, alkylcarbonyl or alkoxycarbonyl, X₁ is halogen, alkyl,haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy,haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy,alkylthio, haloalkyithio, alkenylthio, haloalkenylthio, alkynylthio,haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which maybe substituted by Y₁,phenoxy which may be substituted by Y₁,benzyloxywhich may be substituted by Y₁ or pyridyloxy which may be substituted byY₁,and Y₁ is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio,haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,haloalkylsulfonyl, dialkylaminosulfonyl, nitro or cyano.
 2. The acidamide derivative or a salt thereof according to claim 1, wherein A isphenyl which may be substituted by X′, X′ is alkoxyalkoxy,haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, phenyl whichmay be substituted by Y′, phenoxy which may be substituted by Y′,benzyloxy which may be substituted by Y′, pyridyloxy which may besubstituted by Y′, —OR₄, —SR₅, —NR₆R₇, —CO₂R₈, —C(═O)NR₉R₁₀ or anunsaturated heterocyclic group (the unsaturated heterocyclic ring may besubstituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), and Y′is —OR₄, —CO₂R₁₁, —CONR₁₂R₁₃ or an unsaturated heterocyclic group (theunsaturated heterocyclic ring may be substituted by halogen, alkyl,haloalkyl, alkoxy or haloalkoxy).
 3. The acid amide derivative or a saltthereof according to claim 1, wherein R₁ is alkyl, cyano or —CO₂R₁₄, R₂is alkyl, cyano or —CO₂R₁₄, R₁₄ is hydrogen or alkyl, R₃ is hydrogen,alkyl, alkoxyalkyl, alkylthioalkyl, —COR₁₅, —S(O)_(m)R₁₆ or R₁₅ ishydrogen, alkyl or alkoxy, R₁₆ is alkyl, haloalkyl or phenyl, R₁₇ isalkyl, haloalkyl or phenyl, R₁₈ is alkyl, haloalkyl or phenyl, m is from0 to 2, and n is 0 to
 2. 4. The acid amide derivative or a salt thereofaccording to claim 1, wherein B is a heterocyclic group which may besubstituted by Y.
 5. The acid amide derivative or a salt thereofaccording to claim 1, wherein A is a phenyl group substituted with a4-bromo substituent, B is a 2-thienyl group, R₁ and R₂ are methyl, andR₃ is hydrogen.
 6. The acid amide derivative or a salt thereof accordingto claim 1, wherein A is phenyl.
 7. The acid amide derivative or a saltthereof according to claim 1, wherein A is phenyl substituted by X.
 8. Aprocess for producing an acid amide derivative of the formula (I) or asalt thereof:

wherein A is phenyl which may be substituted by X, B is a heterocyclicgroup which may be substituted by Y, or a fused heterocyclic group whichmay be substituted by Y, X is halogen, alkyl, haloalkyl, alkenyl,haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkoxyalkoxy,haloalkoxyalkoxy, alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, alkenyloxy,haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio,alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio,alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, phenyl which may be substituted byY, phenoxy which may be substituted by Y, benzyloxy which may besubstituted by Y, pyridyloxy which may be substituted by Y, —OR₄, —SR₅,—NR₆R₇, —CO₂R₈, —C(═O)NR₉R₁₀ or an unsaturated heterocyclic group (theunsaturated heterocyclic ring may be substituted by halogen, alkyl,haloalkyl, alkoxy or haloalkoxy), Y is halogen, alkyl, haloalkyl,alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl,haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,dialkylaminosulfonyl, nitro, cyano, —OR₄, —CO₂R₁₁, —CONR₁₂R₁₃ or anunsaturated heterocyclic group (the unsaturated heterocyclic ring may besubstituted by halogen, alkyl, haloalkyl, alkoxy or haloalkoxy), each ofR₁ and R₂ is alkyl, cyano or —CO₂R₁₄,or R₁ and R₂ may together form a 3-to 6-membered saturated carbocyclic ring, R₃ is hydrogen, alkyl,alkoxyalkyl, alkylthioalkyl, —COR₁₅, —S(O)_(m)R₁₆ or —S(O)_(n)NR₁₇R₁₈,each of R₄ and R₆ is hydrogen, —C(═W)R₁₉, —C(═W)OR₂₀, —C(═W)SR₂₁,—C(═W)NR₂₂R₂₃, —S(O)_(q)R₂₄ or —S(O)rNR₂₅R₂₆, R₅ is hydrogen, —C(═W)R₁₉,—C(═W)OR₂₀, —C(═W)SR₂₁ or —C(═W)NR₂₂R₂₃, R₇ is hydrogen, alkyl orhaloalkyl, each of R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₃ and R₁₄ is hydrogen oralkyl, R₁₅ is hydrogen, alkyl or alkoxy, each of R₁₆, R₁₇, R₁₈, R₁₉,R₂₀, R₂₁, R₂₂, R₂₃, R₂₄, R₂₅ and R₂₆ is alkyl, haloalkyl or phenyl,wherein the phenyl which may be substituted by halogen, alkyl,haloalkyl, alkoxy or haloalkoxy, each of m, n, q and r is from 0 to 2,and W is oxygen or sulfur, provided that following is excluded: A isphenyl which may be substituted by X₁ B is pyridyl which may besubstituted by Y₁ or pyrazolyl which may be substituted by Y₁, each ofR₁ and R₂ is alkyl, or R₁ and R₂ together form a 3- to 6-memberedsaturated carbocyclic ring, R₃ is hydrogen, alkyl, alkoxyalkyl,alkylthioalkyl, alkylcarbonyl or alkoxycarbonyl, X₁ is halogen, alkyl,haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy,haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy,alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio,haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl which maybe substituted by Y₁, phenoxy which may be substituted by Y₁, benzyloxywhich may be substituted by Y₁ or pyridyloxy which may be substituted byY₁, and Y₁ is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio,haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,haloalkylsulfonyl, dialkylaminosulfonyl, nitro or cyano.
 9. A pesticidewhich contains the acid amide derivative or a salt thereof as defined inclaim 1 as an active ingredient.
 10. An agricultural or horticulturalpesticide which contains the acid amide derivative or a salt thereof asdefined in claim 1 as an active ingredient.
 11. An insecticide, miticideor nematicide which contains an acid amide derivative or a salt thereofas defined in claim 1 as an active ingredient.
 12. A nematicide whichcontains an acid amide derivative or a salt thereof as defined in claim1 as an active ingredient.
 13. An agent for controlling parasites onanimals, which contains an acid amide derivative or a salt thereof asdefined in claim 1 as an active ingredient.
 14. An agent for controllingparasites in the bodies of animals, which contains an acid amidederivative or a salt thereof as defined in claim 1 as an activeingredient.
 15. An agent for preventing or curing animal diseases causedby parasites, which contains an acid amide derivative or a salt thereofas defined in claim 1 as an active ingredient.
 16. A method forcontrolling a pest, which comprises using an effective amount of an acidamide derivative or a salt thereof as defined in claim 1.